Stereocontrolled Construction of Arrays of Stereogenic Centers: The Mullins Synthesis of (-)-Lasiol

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Aldol Condensation ◽  
Catalyst System ◽  
Geometric Isomer ◽  
Ni Catalyst ◽  
University Of Texas ◽  
Enantioselective Epoxidation ◽  
Institute Of Technology ◽  
Tandem Cyclization ◽  
Catalyst Systems ◽  
The University

Hisashi Yamamoto of the University of Chicago devised (J. Am. Chem. Soc. 2010, 132, 7878) catalyst systems for the enantioselective epoxidation of a Z -homoallylic alcohol 1. Michael J. Krische of the University of Texas developed (J. Am. Chem. Soc. 2010, 132, 1760) a catalyst system for the highly stereoselective addition of the vinyl acetal 5 to an aldehyde 4. Joëlle Prunet of the University of Glasgow showed (Tetrahedron Lett. 2010, 51, 256) that the tandem cyclization/Julia olefination from 7 also proceeded with high stereocontrol. Professor Yamamoto established (J. Am. Chem. Soc. 2010, 132, 5354) that depending on conditions, the aldol condensation of 10 could be directed selectively toward either diastereomer of the product 12. James M. Takacs of the University of Nebraska effected (J. Am. Chem. Soc. 2010, 132, 1740) the enantioselective hydroboration of 10. The other geometric isomer of 10 gave the alternative diastereomer of 12, also with high ee. John Limanto and Shane W. Krska of Merck Process optimized (Organic Lett . 2010, 12, 512) the dynamic kinetic reduction of 13 , giving 14 with excellent diastereocontrol. Professor Krische extended (J. Am. Chem. Soc. 2010, 132, 4562) his reductive homologation to the (racemic) carbonate 15, delivering 16 with excellent dr and ee. Hirokazu Urabe of the Tokyo Institute of Technology showed (Organic Lett. 2010, 12, 1012) that a Grignard reagent under iron catalysis opened the epoxide 17, readily available by Jørgensen-Cordova epoxidation followed by homologation, with clean inversion and high regiocontrol. Fraser F. Fleming of Duquesne University developed (Organic Lett. 2010, 12, 3030) a general route to quaternary alkylated centers by alkylation of nitriles such as 19. Shigeki Matsunaga and Masakatsu Shibasaki of the University of Tokyo devised (J. Am. Chem. Soc. 2010, 132, 3666) a Ni catalyst for the stereoselective conjugate addition of the lactam 22 to a nitroalkene 21. Aldehydes can also be added to nitroalkenes with high dr and ee, as illustrated by the conversion of 24 to 26 reported (J. Am. Chem. Soc. 2010, 132, 50) by Bukuo Ni of Texas A&M University, Commerce.

Construction of Single Stereocenters

2017 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Asymmetric Hydrogenation ◽  
Bifunctional Catalyst ◽  
Allyl Ether ◽  
University Of Texas ◽  
Iridium Catalysis ◽  
Enantioselective Epoxidation ◽  
Institute Of Technology ◽  
The University ◽  
Academy Of Sciences ◽  
University Of Manchester

Haifeng Du at the Chinese Academy of Sciences reported (J. Am. Chem. Soc. 2013, 135, 6810) the borane-catalyzed asymmetric hydrogenation of imine 1 to 2 using the diene 3 as a chiral ligand for boron. A single-enzyme cascade for the reductive transam­ination of acetophenone 4 with amine 5 to produce enantiopure sec-phenethylamine 6 was developed (Chem. Commun. 2013, 49, 161) by Per Berglund at the KTH Royal Institute of Technology in Sweden. A group at Boehringer Ingelheim in Ridgefield, Connecticut, led by Jonathan T. Reeves, disclosed (J. Am. Chem. Soc. 2013, 135, 5565) a procedure for the addition of DMF anion to N-sulfinyl imine 7 to furnish tert-leucine amide 8 with high diastereoselectivity. The tertiary carbinamine 10 was synthesized (Org. Lett. 2013, 15, 34) via the carbolithiation/rearrangement of vinyl­urea 9 as reported by Jonathan Clayden at the University of Manchester. Gregory C. Fu at Caltech reported (Angew. Chem. Int. Ed. 2013, 52, 2525) that the chiral phosphine 12 catalyzed the enantioselective addition of trifluoroacetamide to allene 11 to produce γ-amino ester 13 in enantioenriched form. Adeline Vallribera at the Autonomous University of Barcelona found (Org. Lett. 2013, 15, 1448) that a euro­pium pybox complex effected the highly enantioselective α-amination of β-ketoester 14 to generate 15 on the way to the Parkinson’s disease co-drug L-carbidopa. Hisashi Yamamoto at the University of Chicago and Chubu University reported (J. Am. Chem. Soc. 2013, 135, 3411) that a halfnium(IV) complex of the bishydroxamic acid 17 catalyzed the enantioselective epoxidation of the tertiary homoallylic alcohol 16 to 18. The rearrangement of the allylic carbonate 19 to produce allyl ether 21 with high ee under iridium catalysis in the presence of ligand 20 was disclosed (Org. Lett. 2013, 15, 512) by Hyunsoo Han at the University of Texas, San Antonio. The asymmetric vinylogous aldol reaction of 3-methyl-2-cyclohexen-1-one 22 and α-keto ester 23 to furnish tertiary carbinol 25 using the bifunctional catalyst 24 was developed (Org. Lett. 2013, 15, 220) by Paolo Melchiorre at ICREA and ICIQ in Spain.

Establishing Arrays of Stereogenic Centers: The Sato/Chida Synthesis of (-)-Kainic Acid

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Catalyst System ◽  
Allylic Alcohol ◽  
University Of Pennsylvania ◽  
Ni Catalyst ◽  
Max Planck ◽  
Stereogenic Centers ◽  
University College London ◽  
Enantioselective Addition ◽  
La Jolla ◽  
The University

Benjamin List of the Max-Planck-Institut, Mülheim, devised (J. Am. Chem. Soc. 2010, 132, 10227) a catalyst system for the stereocontrolled epoxidation of a trisubstituted alkenyl aldehyde 1. Takashi Ooi of Nagoya University effected (Angew. Chem. Int. Ed. 2010, 49, 7562; see also Org. Lett. 2010, 12, 4070) enantioselective Henry addition to an alkynyl aldehyde 3. Madeleine M. Joullié of the University of Pennsylvania showed (Org. Lett. 2010, 12, 4244) that an amine 7 added selectively to an alkynyl aziridine 6. Yutaka Ukaji and Katsuhiko Inomata of Kanazawa University developed (Chem. Lett. 2010, 39, 1036) the enantioselective dipolar cycloaddition of 9 with 10. K. C. Nicolaou of Scripps/La Jolla observed (Angew. Chem. Int. Ed. 2010, 49, 5875; see also J. Org. Chem. 2010, 75, 8658) that the allylic alcohol from enantioselective reduction of 12 could be hydrogenated with high diastereocontrol. Masamichi Ogasawara and Tamotsu Takahashi of Hokkaido University added (Org. Lett. 2010, 12, 5736) the allene 14 to the acetal 15 with substantial stereocontrol. Helen C. Hailes of University College London investigated (Chem. Comm. 2010, 46, 7608) the enzyme-mediated addition of 18 to racemic 17. Dawei Ma of the Shanghai Institute of Organic Chemistry, in the course of a synthesis of oseltamivir (Tamiflu), accomplished (Angew. Chem. Int. Ed. 2010, 49, 4656) the enantioselective addition of 21 to 20. Shigeki Matsunaga of the University of Tokyo and Masakatsu Shibasaki of the Institute of Microbial Chemistry developed (Org. Lett. 2010, 12, 3246) a Ni catalyst for the enantioselective addition of 23 to 24. Juthanat Kaeobamrung and Jeffrey W. Bode of ETH-Zurich and Marisa C. Kozlowski of the University of Pennsylvania devised (Proc. Natl. Acad. Sci. 2010, 107, 20661) an organocatalyst for the enantioselective addition of 27 to 26. Yihua Zhang of China Pharmaceutical University and Professor Ma effected (Tetrahedron Lett. 2010, 51, 3827) the related addition of 27 to 29. There have been scattered reports on the stereochemical course of the coupling of cyclic secondary organometallics. In a detailed study, Paul Knochel of Ludwig-Maximilians- Universität München showed (Nat. Chem. 2020, 2, 125) that equatorial bond formation dominated, exemplified by the conversion of 31 to 33.

Best Synthetic Methods: C-C Bond Construction

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Allylic Alcohol ◽  
Synthetic Methods ◽  
Grignard Reagents ◽  
Ni Catalyst ◽  
University Of Texas ◽  
University Of British Columbia ◽  
Terminal Alkene ◽  
Major Producer ◽  
The University ◽  
Linear Product

Nobuaki Kambe of Osaka University found (Tetrahedron Lett. 2009, 50, 5644) that with a Ni catalyst, Grignard reagents coupled preferentially with primary alkyl iodides, even in the presence of the usually reactive ketone. Maurice Santelli of the Université d’Aix-Marseille devised (Tetrahedron Lett. 2009, 50, 5238) a protocol for the conversion of a ketal 4 to the doubly homologated product 6. Brian T. Gregg of AMRI established (Tetrahedron Lett. 2009, 50, 3978; Tetrahedron Lett. 2009, 50, 7070) a procedure for the homologation of a nitrile 7 to the amine 9. Replacement of the NaBH4 with a second Grignard reagent led to the α-quaternary amine (not shown). Toshiaki Murai of Gifu University independently developed (J. Org. Chem. 2009, 74, 5703) a protocol for coupling two Grignard reagents with the linchpin reagent 11 to give the amine 12. Laurel L. Schafer of the University of British Columbia demonstrated (Angew. Chem. Int. Ed. 2009, 48, 8361) Ta-catalyzed intramolecular addition of a methyl amine 14 to the terminal alkene 13 to give 15. Jason S. Kingsbury of Boston College extended (Organic Lett. 2009, 11, 3202) the Roskamp protocol to unstable diazo alkanes such as 17, to give 18. Katsukiyo Miura of Saitama University found (Organic Lett. 2009, 11, 5066) that Pt catalyzed the branched addition of a terminal alkenyl silane 19 to an aldehyde 16 to give the branched adduct 20. Silanes such as 19 are readily prepared directly from the corresponding terminal alkene. Kálmán J. Szabó of Stockholm University observed (J. Org. Chem. 2009, 74, 5695) that the allyl boronate derived from the allylic alcohol 21 could add to the aldehyde 23 to give, depending on the solvent, either the branched product 24 or the linear product 25. The Wittig reaction is a major producer of by-product waste in chemical synthesis. Yong Tang of the Shanghai Institute of Organic Chemistry found (J. Org. Chem. 2007, 72, 6628) that Ph3As could serve catalytically in the condensation of 26 with an aldehyde. Christopher J. O’Brien of the University of Texas at Arlington and Gregory A. Chass of the University of Wales described (Angew. Chem. Int. Ed. 2009, 48, 6836) a related procedure using a cyclic phosphine.

Functional Group Transformations

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Gold Catalyst ◽  
Sulfonyl Chloride ◽  
Allylic Alcohol ◽  
West Virginia University ◽  
Israel Institute ◽  
University Of Texas ◽  
Amino Amide ◽  
Cu Catalyst ◽  
Institute Of Technology ◽  
The University

Mark Gandelman of the Technion–Israel Institute of Technology devised (Adv. Synth. Catal. 2011, 353, 1438) a protocol for the decarboxylative conversion of an acid 1 to the iodide 3. Doug E. Frantz of the University of Texas, San Antonio effected (Angew. Chem. Int. Ed. 2011, 50, 6128) conversion of a β-keto ester 4 to the diene 5 by way of the vinyl triflate. Pei Nian Liu of the East China University of Science and Technology and Chak Po Lau of the Hong Kong Polytechnic University (Adv. Synth. Catal. 2011, 353, 275) and Robert G. Bergman and Kenneth N. Raymond of the University of California, Berkeley (J. Am. Chem. Soc. 2011, 133, 11964) described new Ru catalysts for the isomerization of an allylic alcohol 6 to the ketone 7. Xiaodong Shi of West Virginia University optimized (Adv. Synth. Catal. 2011, 353, 2584) a gold catalyst for the rearrangement of a propargylic ester 8 to the enone 9. Xue-Yuan Liu of Lanzhou University used (Adv. Synth. Catal. 2011, 353, 3157) a Cu catalyst to add the chloramine 11 to the alkyne 10 to give 12. Kasi Pitchumani of Madurai Kamaraj University converted (Org. Lett. 2011, 13, 5728) the alkyne 13 into the α-amino amide 15 by reaction with the nitrone 14. Katsuhiko Tomooka of Kyushu University effected (J. Am. Chem. Soc. 2011, 133, 20712) hydrosilylation of the propargylic ether 16 to the alcohol 17. Matthew J. Cook of Queen’s University Belfast (Chem. Commun. 2011, 47, 11104) and Anna M. Costa and Jaume Vilarrasa of the Universitat de Barcelona (Org. Lett. 2011, 13, 4934) improved the conversion of an alkenyl silane 18 to the iodide 19. Vinay Girijavallabhan of Merck/Kenilworth developed (J. Org. Chem. 2011, 76, 6442) a Co catalyst for the Markovnikov addition of sulfide to an alkene 20. Hojat Veisi of Payame Noor University oxidized (Synlett 2011, 2315) the thiol 22 directly to the sulfonyl chloride 23. Nicholas M. Leonard of Abbott Laboratories prepared (J. Org. Chem. 2011, 76, 9169) the chromatography-stable O-Su ester 25 from the corresponding acid 24.

Organocatalyzed C–C Ring Construction: The Bradshaw/Bonjoch Synthesis of (−)-Cermizine B

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
San Antonio ◽  
Bond Formation ◽  
Bryn Mawr ◽  
National Chemical Laboratory ◽  
Chemical Laboratory ◽  
Enantiomerically Pure ◽  
University Of Texas ◽  
National University ◽  
Institute Of Technology ◽  
The University

In a continuation of his studies (OHL20141229, OHL20140811) of organocatalyzed 2+2 photocycloaddition, Thorsten Bach of the Technische Universität München assembled (Angew. Chem. Int. Ed. 2014, 53, 7661) 3 by adding 2 to 1. Li-Xin Wang of the Chengdu Institute of Organic Chemistry also used (Org. Lett. 2014, 16, 6436) an organocatalyst to effect the addition of 5 to 4 to give 6. Shuichi Nakamura of the Nagoya Institute of Technology devised (Org. Lett. 2014, 16, 4452) an organocatalyst that mediated the enantioselective opening of the aziridine 7 to 8. Zhi Li of the National University of Singapore cloned (Chem. Commun. 2014, 50, 9729) an enzyme from Acinetobacter sp. RS1 that reduced 9 to 10. Gregory C. Fu of Caltech developed (Angew. Chem. Int. Ed. 2014, 53, 13183) a phosphine catalyst that directed the addition of 12 to 11 to give 13. Armido Studer of the Westfälische Wilhelms-Universität Münster showed (Angew. Chem. Int. Ed. 2014, 53, 9622) that 15 could be added to 14 to give 16 in high ee. Akkattu T. Biju of CSIR-National Chemical Laboratory described (Chem. Commun. 2014, 50, 14539) related results. The photostimulated enantioselective ketone alkylation developed (Chem. Sci. 2014, 5, 2438) by Paolo Melchiorre of ICIQ was powerful enough to enable the alkyl­ation of 17 with 18 to give 19, overcoming the stereoelectronic preference for axial bond formation. David W. Lupton of Monash University established (J. Am. Chem. Soc. 2014, 136, 14397) the organocatalyzed transformation of the dienyl ester 20 to 21. James McNulty of McMaster University added (Angew. Chem. Int. Ed. 2014, 53, 8450) azido acetone 23 to 22 to give 24 in high ee. There are sixteen enantiomerically-pure diastereomers of the product 27. John C.-G. Zhao of the University of Texas at San Antonio showed (Angew. Chem. Int. Ed. 2014, 53, 7619) that with the proper choice of organocatalyst, with or without subsequent epimerization, it was possible to selectively prepare any one of eight of those diastereomers by the addition of 26 to 25. William P. Malachowski of Bryn Mawr College showed (Tetrahedron Lett. 2014, 55, 4616) that 28, readily prepared by a Birch reduction protocol, was converted by heating followed by exposure to catalytic Me3P to the angularly-substituted octalone 29.

Reactions of Alkenes: The RajanBabu Synthesis of Pseudopterosin G-J Aglycone Dimethyl Ether

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Medical Center ◽  
Selective Reduction ◽  
Oxidative Cleavage ◽  
University Of Texas ◽  
Furman University ◽  
National University ◽  
Institute Of Technology ◽  
Seoul National University ◽  
The University ◽  
Medical University

Xiangge Zhou of Sichuan University showed (Tetrahedron Lett. 2011, 52, 318) that even the monosubstituted alkene 1 was smoothly converted to the methyl ether 2 by catalytic FeCl3. Brian C. Goess of Furman University protected (J. Org. Chem. 2011, 76, 4132) the more reactive alkene of 3 as the 9-BBN adduct, allowing selective reduction of the less reactive alkene to give, after reoxidation, the monoreduced 4. Nobukazu Taniguchi of the Fukushima Medical University added (Synlett 2011, 1308) Na p-toluenesulfinate oxidatively to 1 to give the sulfone 5. Krishnacharya G. Akamanchi of the Indian Institute of Chemical Technology, Mumbai oxidized (Synlett 2011, 81) 1 directly to the bromo ketone 6. Osmium is used catalytically both to effect dihydroxylation, to prepare 8, and to mediate oxidative cleavage, as in the conversion of 7 to the dialdehyde 9. Ken-ichi Fujita of AIST Tsukuba devised (Tetrahedron Lett. 2011, 52, 3137) magnetically retrievable osmium nanoparticles that can be reused repeatedly for the dihydroxylation. B. Moon Kim of Seoul National University established (Tetrahedron Lett. 2011, 52, 1363) an extraction scheme that allowed the catalytic Os to be reused repeatedly for the oxidative cleavage. Maurizio Taddei of the Università di Siena showed (Synlett 2011, 199) that aqueous formaldehyde could be used in place of Co/H2 (syngas) for the formylation of 1 to 10. Hirohisa Ohmiya and Masaya Sawamura of Hokkaido University prepared (Org. Lett. 2011, 13, 1086) carboxylic acids (not illustrated) from alkenes using CO2. Joseph M. Ready of the University of Texas Southwestern Medical Center selectively arylated (Angew. Chem. Int. Ed. 2011, 50, 2111) the homoallylic alcohol 11 to give 12. Many reactions of alkenes are initiated by hydroboration, then conversion of the resulting alkyl borane. Hiroyuki Kusama of the Tokyo Institute of Technology photolyzed (J. Am. Chem. Soc. 2011, 133, 3716) 14 with 13 to give the ketone 15. William G. Ogilvie of the University of Ottawa added (Synlett 2011, 1113) the 9-BBN adduct from 1 to 16 to give 17. Professors Ohmiya and Sawamura effected (Org. Lett. 2011, 13, 482) a similar conjugate addition, not illustrated, of 9-BBN adducts to α,β-unsaturated acyl imidazoles.

Heteroaromatic Construction: The Jia Synthesis of (-)- cis -Clavicipitic Acid

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Organic Chemistry ◽  
Aldol Condensation ◽  
Streptomyces Coelicolor ◽  
University Of Florida ◽  
Bacterial Signaling ◽  
Shanghai Institute ◽  
Tokyo Institute ◽  
Institute Of Technology ◽  
The University ◽  
Technological University

Simultaneously, Aaran Aponick of the University of Florida (Organic Lett. 2009, 11, 4624) and Shuji Akai of the University of Shizuoka (Organic Lett. 2009, 11, 5002) reported the Au-mediate conversion of a propargylic diol such as 1 to the furan 2. Pyrroles can also be prepared using the same protocol. Jason K. Sello of Brown University developed (Organic Lett. 2009, 11, 2984) the direct aldol condensation of an acetoacetate 3 with the protected 1,3-dihydroxy acetone 4 to give 5, the methyl ester of a methylenomycin furan (MMF) bacterial-signaling molecule from Streptomyces coelicolor. Nobuharu Iwasawa of the Tokyo Institute of Technology demonstrated (Angew. Chem. Int. Ed. 2009, 48, 8318) that the imine 6 was sufficiently nucleophilic to react with the Rh vinylidene derived from the alkyne 7, leading to the pyrrole 8. Min Shi of the Shanghai Institute of Organic Chemistry extended (J. Org. Chem. 2009, 74, 5983) the reactivity of methylene cyclopropanes to the condensation of the aldehyde 9 with an acyl hydrazide, to give the pyrrole 11. Xue-Long Hou, also of the Shanghai Institute of Organic Chemistry, described (Tetrahedron Lett. 2009, 50, 6944) the Au-mediated reorganization of the alkynyl aziridine 12 to the pyrrole 13. Masahiro Yoshida of the University of Tokushima carried out (Tetrahedron Lett. 2009, 50, 6268) a similar rearrangement under oxidative conditions, giving the iodinated pyrrole 15. André M. Beauchemin of the University of Ottawa showed (Angew. Chem. Int. Ed. 2009, 48, 8325) that under acid catalysis, the oxime 16 cyclized to the pyridine 17. Shunsuke Chiba of Nanyang Technological University developed (J. Am. Chem. Soc. 2009, 131, 12570) the Mn(III)-mediated fusion of a cyclopropanol 18 with an alkenyl azide 19 to deliver the pyridine 20. Kazuaki Shimada of Iwate University found (Tetrahedron Lett. 2009, 50, 6651) that an isotellurazole such as 21, easily prepared from the corresponding alkyne, condensed with another alkyne 22, delivering the pyridine 23 with high regiocontrol. Christopher J. Moody of the University of Nottingham devised (Organic Lett. 2009, 11, 3686) a new route to the 1,2,4-triazine 24 from an α-diazoacetoacetate. He carried 24 on to the pyridine 26 by condensation with norbornadiene 25.

Organic Functional Group Protection and Deprotection

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
University Of California ◽  
Ni Catalyst ◽  
University Of Alabama ◽  
Phenyl Ester ◽  
Aryl Ether ◽  
University Of Toronto ◽  
Boston University ◽  
Aldehydes And Ketones ◽  
Institute Of Technology ◽  
The University

Corey R. J. Stephenson of Boston University devised (Chem. Commun. 2011, 47, 5040) a protocol using visible light for removing the PMB group from 1 to give 2. John F. Hartwig, now at the University of California, Berkeley, developed (Science 2011, 332, 439) a Ni catalyst for the cleavage of the durable aryl ether of 3 to give 4. Mark S. Taylor of the University of Toronto devised (J. Am. Chem. Soc. 2011, 133, 3724) the catalyst 6, which selectively mediated esterifi cation of 5 to 7. Jean-Marie Beau of the Université Paris-Sud added (Chem. Commun. 2011, 47, 2146) Et3 SiH following the Fe-catalyzed deprotection-protection of 8, resulting in clean conversion to the bis ether 9. Mahmood Tajbakhsh of the University of Mazandaran showed (Tetrahedron Lett. 2011, 52, 1260) that guanidine HCl catalyzed the conversion of 10 to 11. Stephen W. Wright of Pfizer/Groton established (Tetrahedron Lett. 2011, 52, 3171) that the new urethane protecting group of 12, stable to many conditions, could be deprotected to 13 under conditions that spared even a Boc group. Matthias Beller of the Leibniz-Institute for Catalysis protected (Chem. Commun. 2011, 47, 2152) the amine 14 as the readily hydrolyzed imidazole 16. Sentaro Okamoto of Kanagawa University found (Org. Lett. 2011, 13, 2626) a simple reagent combination for the removal of the sometimes reluctant sulfonamide from 17. Jordi Burés and Jaume Vilarrasa of the Universitat de Barcelona removed (Angew. Chem. Int. Ed. 2011, 50, 3275) the oxime from 19 by Au-catalyzed exchange with 20. Pengfei Wang of the University of Alabama, Birmingham, designed (J. Org. Chem. 2011, 76, 2040) a range of photochemically removable protecting groups for aldehydes and ketones. Rafael Robles of the University of Granada selectively protected (J. Org. Chem. 2011, 76, 2277) the diol 24 using the reagent created by the activation of 25. Berit Olofsson of Stockholm University prepared (Org. Lett. 2011, 13, 3462) the phenyl ester 28 by exposing 27 to the diaryl iodonium triflate. Kannoth Manheri Muraleedharan of the Indian Institute of Technology, Madras, selectively (Org. Lett. 2011, 13, 1932) esterified 29 to 30 with catalytic SmCl3.

scholarly journals Oxy-Steam Reforming of Natural Gas on Ni Catalysts—A Minireview

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 896
Author(s):  
Magdalena Mosinska ◽  
Malgorzata I. Szynkowska ◽  
Pawel Mierczynski
Keyword(s):  
Natural Gas ◽  
Steam Reforming ◽  
Catalyst System ◽  
Liquefied Natural Gas ◽  
Ni Catalyst ◽  
Process Conditions ◽  
Generation Process ◽  
Sulfur And Nitrogen Compounds ◽  
Catalyst Systems ◽  
Safe Transport

Nowadays, the reforming of natural gas is the most common of hydrogen or syngas generation process. Each reforming process leads to the achievement of specific goals and benefits related to investment costs. The disadvantage of the reforming process is the need to preclean it mostly from the sulfur and nitrogen compounds. The solution to this problem may be liquefied natural gas (LNG). Liquefied natural gas has recently been seen as an energy source and may be a promising replacement for natural gas. The constant development of the pipeline network, safe transport and a lot of advantages of LNG were contributed to the research development related to the usage of LNG in energy generation technologies. The presented review is a literature discussion on the processing of methane used to produce hydrogen with particular emphasis on the processes of oxy-steam reforming of natural or liquefied natural gas (OSR-LNG). In addition, a key consideration in this article includes Ni catalyst systems used in the oxy-steam reforming of methane or LNG reactions. An analysis of the OSR process conditions, the type of catalyst and the OSR of the methane reaction mechanism may contribute to the development of a modern, cheap catalyst system, which is characterized by high activity and stability in the oxy-steam reforming of natural gas or LNG (OSR-LNG).

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