C–C Bond Construction: The Hou Synthesis of (−)-Brevipolide H

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
University Of Illinois ◽  
University Of Texas ◽  
Heck Cyclization ◽  
University Of Technology ◽  
Propargylic Alcohol ◽  
Irkutsk Institute ◽  
Aqueous Conditions ◽  
The University

Yao Fu and Lei Liu of the University of Science and Technology of China devised (Chem. Eur. J. 2014, 20, 15334) conditions for the coupling of a halide 2 with a tosyl­ate 1 with inversion of absolute configuration, leading to 3. Hegui Gong of Shanghai University coupled (J. Am. Chem. Soc. 2014, 136, 17645) the glucosyl bromide 4 with an anhydride 5 to give the ketone 6. Luigi Vaccaro of the Università di Perugia showed (Org. Lett. 2014, 16, 5721) that TBAF promoted the opening of the epoxide 7 with the ketene silyl acetal 8, leading to the lactone 9. Valérie Desvergnes and Yannick Landais of the University of Bordeaux assembled (Chem. Eur. J. 2014, 20, 9336) the diketone 12 by using a Stetter catalyst to promote the conjugate addition of the acyl silane 11 to the enone 10. Thomas Werner of the Leibniz-Institute for Catalysis reported (Eur. J. Org. Chem. 2014, 6873) the enantioselective conversion of the prochiral triketone 13 to the bicyclic enone 15 by an intramolecular Wittig reaction, mediated by 14. Elizabeth H. Krenske of the University of Queensland and Christopher J. O’Brien also reported (Angew. Chem. Int. Ed. 2014, 53, 12907) progress (not illustrated) on catalytic Wittig reactions. Michael J. Krische of the University of Texas showed (J. Am. Chem. Soc. 2014, 136, 11902) that Ru-mediated addition of 17 to the aldehyde derived in situ from 16 gave 18 with high Z-selectivity. Vladimir Gevorgyan of the University of Illinois at Chicago constructed (J. Am. Chem. Soc. 2014, 136, 17926) the trisubstituted alkene 20 by the intramolecular Heck cyclization of 19. Kálmán J. Szabó of Stockholm University opti­mized (Chem. Commun. 2014, 50, 9207) the Pd-catalyzed borylation of the alkene 21 followed by in situ addition to the aldehyde 22 to give 23. Boris A. Trofimov of the Irkutsk Institute of Chemistry Siberian Branch devel­oped (Eur. J. Org. Chem. 2014, 4663) aqueous conditions for the preparation of a propargylic alcohol 26 by the addition of an alkyne 25 to the ketone 24. Huanfeng Jiang of the South China University of Technology prepared (Angew. Chem. Int. Ed. 2014, 53, 14485) the alkyne 28 by the oxidative elimination of the tosylhydrazone 27.

Preparation of Heteroaromatic Derivatives

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Ring Expansion ◽  
University Of Pennsylvania ◽  
Au Catalyst ◽  
University Of Illinois ◽  
Oxidative Rearrangement ◽  
University Of Technology ◽  
Acidic Conditions ◽  
The University ◽  
École Polytechnique ◽  
Pais Vasco

Several new routes to furans and to pyrroles have recently been put forward. Inspired by the Achmatowicz ring expansion, Patrick J. Walsh of the University of Pennsylvania developed (J. Am. Chem. Soc. 2008, 130, 4097) the oxidative rearrangement of 3-hydrox-alkyl furans such as 1 to the 3-aldehyde 2. José M. Aurrecoechea of the Universidad del País Vasco established (J. Org. Chem. 2008, 73, 3650) that cumulated alcohols, available by reduction of alkynes such as 3 with SmI2, rearrange under Pd catalysis, and then add to an acceptor alkene such as 4, to give the furan 5. Vladimir Gevorgyan of the University of Illinois at Chicago used (J. Am. Chem. Soc. 2008, 130, 1440) an Au catalyst to rearrange an allene such as 6 to the bromo furan 7. Fabien L. Gagosz of the Ecole Polytechnique, Palaiseau, also found (Organic Lett. 2007, 9, 3181) that an Au catalyst rearranged the eneyne 8 to the pyrrole 9. Azido esters such as 10 are readily prepared from the corresponding aldehyde by phosphonate condensation. Shunsuke Chiba and Koichi Narasaka of Nanyang Technology University demonstrated (Organic Lett. 2008, 10, 313) that thermal condensation of 10 with acetyl acetone 11 gave the pyrrole 12, while Cu catalyzed condensation with acetoacetate 13 gave the complementary pyrrole 14. Huan-Feng Jiang of South China University of Technology observed (Tetrahedron Lett. 2008, 49, 3805) that condensation of an acid chloride 15 with an alkyne 16, presumably to give the alkynyl ketone, followed by the addition of hydrazine delivered the pyrazole 17. Masanobu Uchiyama of RIKEN and Florence Mongin of the Université de Rennes 1 established (J. Org. Chem. 2008, 73, 177) that a pre-formed pyrazole 18 could be metalated and then iodinated, to give 19. Xiaohu Deng of Johnson & Johnson, San Diego reported (Organic Lett. 2008, 10, 1307; J. Org. Chem. 2008, 73, 2412) complementary routes to pyrazoles, combining 20 and 21 under acidic conditions to give 22, and under basic conditions to give 23.

Metal-Mediated Carbocyclic Construction: The Simpkins Synthesis of Ialibinones A and B

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Gold Catalyst ◽  
Conjugate Addition ◽  
South Florida ◽  
Pt Catalyst ◽  
General Strategy ◽  
Ru Catalyst ◽  
University Of Technology ◽  
Rh Catalyst ◽  
Institute Of Technology ◽  
The University

Adriaan J. Minnaard and Ben L. Feringa of the University of Groningen devised (J. Am. Chem. Soc. 2010, 132, 14349) what promises to be a general strategy for the construction of enantiomerically pure cyclopropanes, based on conjugate addition to acceptors such as 1 . X. Peter Zhang of the University of South Florida developed (J. Am. Chem. Soc. 2010, 132, 12796) a Co catalyst for the enantioselective cyclopropanation of α-olefins such as 3. Seiji Iwasa of Toyohashi University of Technology designed (Angew. Chem. Int. Ed. 2010, 49, 8439) a resin-bound Ru catalyst that could be used repeatedly for the enantioselective cyclization of the ester 6. Rai-Shung Lin of National Tsing-Hua University showed (Angew. Chem. Int. Ed. 2010, 49, 9891) that a gold catalyst could expand the alkyne 8 to the cyclobutene 9. Takao Ikariya of the Tokyo Institute of Technology reported (J. Am. Chem. Soc. 2010, 132, 16637) a detailed study of the enantioselective conjugate addition of malonate 11 to cyclopentenone 10. Vladimir A. D’yakonov of the Russian Academy of Sciences, Ufa, showed (Tetrahedron Lett. 2010, 51, 5886) that a cyclic alkyne 13 could be annulated to the cyclopentenone 14. Shunichi Hashimoto of Hokkaido University also designed (Angew. Chem. Int. Ed. 2010, 49, 6979) a resin-bound Rh catalyst that could also be used repeatedly for the enantioselective cyclization of the ester 15. Tushar Kanti Chakraborty of the Central Drug Research Institute used (Tetrahedron Lett. 2010, 51, 4425) Ti(III) to mediate the diastereoselective cyclization of 17 to 18. Alexandre Alexakis of the University of Geneva extended (Synlett 2010, 1694) enantioselective conjugate addition of isopropenyl to the more difficult enone 19. Joseph P. A. Harrity of the University of Sheffield showed (Org. Lett. 2010, 12, 4832) that Pd could catalyze the rearrangement of 21 to 22. Strategies for the controlled construction of polycyclic ring systems are also important. Günter Helmchen of the Universität Heidelberg showed (J. Org. Chem. 2010, 75, 7917) that 23 was efficiently cyclized to the diene with Pt catalyst. The reaction could be carried out in the presence of the dienophile 24 to give 25 directly.

Metal-Mediated C–C Ring Construction: The Carreira Synthesis of (+)-Asperolide C

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Ring Expansion ◽  
Ethyl Acrylate ◽  
Heck Cyclization ◽  
University Of Oxford ◽  
Silyl Enol Ether ◽  
Emory University ◽  
Institute Of Technology ◽  
The University ◽  
Technological University

Djamaladdin G. Musaev and Huw M. L. Davies of Emory University effected (Chem. Sci. 2013, 4, 2844) enantioselective cyclopropanation of ethyl acrylate 2 with the α-diazo ester 1 to give 3 in high ee. Philippe Compain of the Université de Strasbourg used (J. Org. Chem. 2013, 78, 6751) SmI2 to cyclize 4 to the cyclobutanol 5. Jianrong (Steve) Zhou of Nanyang Technological University effected (Chem. Commun. 2013, 49, 11758) enantioselective Heck addition of 7 to the prochiral ester 6 to give the cyclopentene 8. Liu-Zhu Gong of USTC, Hefei added (Org. Lett. 2013, 15, 3958) the Rh enolate from the enantioselective ring expansion of the α-diazo ester 9 to the nitroalkene 10, to give 11 in high de. Stephen P. Fletcher of the University of Oxford set (Angew. Chem. Int. Ed. 2013, 52, 7995) the cyclic quaternary center of 14 by the enantioselective conjugate addition to 12 of the alkyl zirconocene derived from 13. Alexandre Alexakis of the University of Geneva reported (Chem. Eur. J. 2013, 19, 15226) high ee from the conjugate addition of alkenyl Al reagents (not illustrated) to 12. Paultheo von Zezschwitz of Philipps-Universität Marburg prepared (Adv. Synth. Catal. 2013, 355, 2651) the silyl enol ether 17 by trapping the intermediate from the conjugate addition of 16 to 15. Stefan Bräse of the Karlsruhe Institute of Technology effected (Eur. J. Org. Chem. 2013, 7110) conjugate addition to the prochiral dienone 18 to give the highly substi­tuted cyclohexenone 19. Ping Tian and Guo-Qiang Lin of the Shanghai Institute of Organic Chemistry cyclized (J. Am. Chem. Soc. 2013, 135, 11700) 20 to the kinetic, less stable epimer of the diketone 21. Rh-mediated intramolecular C–H insertion has been a powerful tool for the con­struction of cyclopentane derivatives. Douglass F. Taber of the University of Delaware found (J. Org. Chem. 2013, 78, 9772) that the Rh carbene derived from 22 was dis­criminating enough to target the more nucleophilic C–H bond, leading to the cyclohexanone 23. Kozo Shishido of the University of Tokushima observed (Org. Lett. 2013, 15, 3666) high diastereoselectivity in the intramolecular Heck cyclization of 24 to 25.

TEM Studies of Shear Bands in a Bulk Metallic Glass Based Composite

2001 ◽  
Vol 7 (S2) ◽  
pp. 1120-1121
Author(s):  
E. Pekarskaya ◽  
C.P. Kim ◽  
W.L. Johnson
Keyword(s):  
Metallic Glasses ◽  
Shear Bands ◽  
High Yield ◽  
In Situ Tem ◽  
Two Phase ◽  
University Of Illinois ◽  
Glass Forming ◽  
The University ◽  
Very High

In 1980’s the discovery of multicomponent systems with exceptional glass forming ability enabled the synthesis of metallic glasses at relatively low cooling rates, 10−1 — 102 K/s and at a larger thicknesses. Bulk metallic glasses normally have very high yield stress, σy = 0.02 · Y (Y is Young’s modulus), high elastic limit of about 2%, but fail with very little global plasticity, typically along a localized shear band at a 45 degree angle with respect to the applied stress.The material studied in the present work is a two-phase Zr56.3Ti13.8Cu6.9Ni5.6Nb5.0Be12.5 alloy,prepared by in-situ processing. The alloy consists of amorphous and crystalline phases. In-situ TEM straining (tensile) experiments were performed at room temperature in JEOL 4000EX operating at 300kV. The experiments were carried out in the Center for Microanalysis of Materials in the University of Illinois at Urbana-Champaign. The goal of the study was to understand the deformation mechanisms of such composite material.

Preparation of Benzene Derivatives: The Yu/Baran Synthesis of (+)-Hongoquercin A

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Electrophilic Aromatic Substitution ◽  
University Of Michigan ◽  
Aromatic Substitution ◽  
Blocking Group ◽  
University Of Texas ◽  
University Of Houston ◽  
National University ◽  
Reformatsky Reagent ◽  
The University

Lutz Ackermann of the Georg-August-Universität Göttingen oxidized (Org. Lett. 2013, 15, 3484) the anisole derivative 1 to the phenol 2. Melanie S. Sanford of the University of Michigan devised (Org. Lett. 2013, 15, 5428) complementary condi­tions for either para acetoxylation of 3, illustrated, to give 4, or meta acetoxylation. Lukas J. Goossen of the Technische Universität Kaiserlautern developed (Synthesis 2013, 45, 2387) conditions for the cascade alkoxylation/decarboxylation of 5 to give 6. Cheol-Hong Cheon of Korea University showed (J. Org. Chem. 2013, 78, 12154) that the boronic acid of 7 could act as a blocking group during electrophilic aromatic substitution or, as illustrated, as an ortho directing group. It could then be removed by protodeboronation, leading to 8. Jun Wu of Zhejiang University coupled (Synlett 2013, 24, 1448) the phenol 9 with the bromo amide 10 to give an ether that, on exposure to KOH at elevated temperature, rearranged to the intermediate amide, that was then hydrolyzed to 11. Dong-Shoo Shin of Changwon National University reported (Tetrahedron Lett. 2013, 54, 5151) a similar protocol (not illustrated) to prepare unsubsti­tuted anilines. Guangbin Dong of the University of Texas, Austin used (J. Am. Chem. Soc. 2013, 135, 18350) a variation on the Catellani reaction to add 13 to the ortho bromide 12 to give the meta amine 14. Kei Manabe of the University of Shizuoka found (Angew. Chem. Int. Ed. 2013, 52, 8611) that the crystalline N-for­myl saccharin 16 was a suitable CO donor for the carbonylation of the bromide 15 to the aldehyde 17. John F. Hartwig of the University of California, Berkeley described (J. Org. Chem. 2013, 78, 8250) the coupling of the zinc enolate of an ester (Reformatsky reagent), either preformed or generated in situ, with an aryl bromide 18 to give 19. Olafs Daugulis of the University of Houston developed (Org. Lett. 2013, 15, 5842) conditions for the directed ortho phenoxylation of 20 with 21 to give 22. Yao Fu of the University of Science and Technology of China effected (J. Am. Chem. Soc. 2013, 135, 10630) directed ortho cyanation of 23 with 24 to give 25.

Arrays of Stereogenic Centers: The Thomson Synthesis of (−)-Galactin

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
East China ◽  
Allylic Alcohols ◽  
University Of Texas ◽  
University Of New Mexico ◽  
Homoallylic Alcohols ◽  
Stereogenic Centers ◽  
Normal University ◽  
The University ◽  
Medical University

Hisashi Yamamoto of the University of Chicago and Chubu University developed (J. Am. Chem. Soc. 2014, 136, 1222) a tungsten catalyst for the enantioselective oxida­tion of allylic alcohols such as 1 to the epoxide 2. Homoallylic alcohols also worked well. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry devised (Chem. Eur. J. 2014, 20, 68) a scalable Zn-catalyzed protocol for the coupling of 3 with 4 to give 5. Professor Shibasaki and Takumi Watanabe, also of the Institute of Microbial Chemistry, established (Org. Lett. 2014, 16, 3364) a Nb catalyst for the preparation of 8 by the Henry addition of 7 to 6. Wenhao Hu of East China Normal University effected (Synthesis 2014, 46, 1348) the coupling of 9 and 10 with two equivalents of aniline to give the diamine 10. Sanzhong Luo of the Institute of Chemistry, Beijing showed (Angew. Chem. Int. Ed. 2014, 53, 4149) that the adduct between 11 and an in situ formed N-nitroso could be reduced with high diastereoselectivity, leading to 12. Kumagai and Shibasaki also described (Angew. Chem. Int. Ed. 2014, 53, 5327) the assembly of 15 by the enantiose­lective addition 14 to 13. Bernhard Breit of the Albert-Ludwigs-Universität Freiburg effected (Synthesis 2014, 46, 1311) the carbonylation of the alkene 16 to give an alde­hyde that underwent in situ condensation with the imine 17, leading, after a subse­quent addition of vinyl magnesium chloride, to the lactone 18. Michael J. Krische of the University of Texas prepared (J. Am. Chem. Soc. 2014, 136, 8911) the diol 21 by adding the racemic epoxide 20 to the aldehyde 19. Martin Hiersemann of the Technische Universität Dortmund achieved (J. Org. Chem. 2014, 79, 3040) high enantioselectivity in the rearrangement of the enol ether 22 to 23. Michael T. Crimmins also observed (Org. Lett. 2014, 16, 2458) high ste­reocontrol in the rearrangement of 24 to 25. Wannian Zhang and Chunquan Sheng of the Second Military Medical University and Wei Wang of the University of New Mexico and the East China University of Science and Technology added (Org. Lett. 2014, 16, 692) the diketone 26 to the aldehyde 6 to give an intermediate adduct, that further cyclized to 27.

Organic Functional Group Interconversion

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Carboxylic Acid ◽  
Inner Mongolia ◽  
Terminal Alkyne ◽  
Yale University ◽  
Indiana University ◽  
University Of Texas ◽  
Ru Catalyst ◽  
University Of Technology ◽  
The University ◽  
École Polytechnique

Feng Li of the Nanjing University of Science and Technology devised (Chem. Commun. 2014, 50, 8303) a combination of reagents that directly converted the alcohol 1 to the protected amine 2. Yong-Sheng Bao and Bao Zhaorigetu of Inner Mongolia Normal University selectively (J. Org. Chem. 2014, 79, 6715) demethylated the tertiary amine 4, leading to the amide 5. Christopher W. Bielawski of the University of Texas devel­oped (Chem. Eur. J. 2014, 20, 13487) the reagent 7 for the conversion of an alcohol 6 to the bromide 8. The diiodo analogue of 7 also worked well. Ross Denton of the University of Nottingham showed (Chem. Commun. 2014, 50, 7340) that the reagent 10 efficiently mediated the Mitsunobu coupling of 9 with ben­zoic acid to give 11. The other product of the reaction, Ph₃ P=O, could be converted back to 10. Silas P. Cook of Indiana University established (J. Am. Chem. Soc. 2014, 136, 9521) conditions for the selective conversion of the bromide 12 to the boronate 13. Gwilherm Evano of the Université Libre de Bruxelles converted (Chem. Commun. 2014, 50, 11907) the alkenyl iodide 14 to the nitrile 15 using acetone cyanohydrin as the nitrile anion source. Seth B. Herzon of Yale University developed (Angew. Chem. Int. Ed. 2014, 53, 7892) an improved Ru catalyst for the hydration of a terminal alkyne 16 to the aldehyde 17. Clément Mazet of the University of Geneva used (Chem. Commun. 2014, 50, 10592) an Ir catalyst for the isomerization of a 2,2-disubstituted epoxide 18 to the aldehyde 19. Laurent El Kaïm of the Ecole Polytechnique, Laurence Grimaud of UMPC, and Roland Jacquot and Philippe Marion of Solvay showed (Synthesis 2014, 46, 1802) that in the presence of glutaronitrile 21, AlCl₃ was an effective catalyst for the conversion of an acid 20 to the nitrile 22. Yi-Si Feng and Hua-Jian Xu of the Hefei University of Technology found (Org. Lett. 2014, 16, 4586) that a carboxylic acid 23 could be coupled with diphenyl disul­fide under decarboxylating conditions, leading to the sulfide 24. Kenneth M. Doll of USDA Peoria observed (ACS Catal. 2014, 4, 3517) that decarboxylation of the unsat­urated carboxylic acid 25 with a Ru catalyst delivered the alkene 26 as a mixture of regioisomers.

Construction of Arrays of Stereogenic Centers: The Zhang Synthesis of (+)-Podophyllotoxin

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Organic Chemistry ◽  
Conjugate Addition ◽  
Chiral Auxiliary ◽  
Stanford University ◽  
Enol Ethers ◽  
University Of Technology ◽  
Stereogenic Centers ◽  
Diastereoselective Addition ◽  
University Of Bristol ◽  
The University

Varinder K. Aggarwal of the University of Bristol showed (Angew. Chem. Int. Ed. 2009, 48, 1149) that condensation of a boronic ester 2 with a metalated aziridine 1 led, after oxidation, to the defined amino alcohol 3. Hisashi Yamamoto of the University of Chicago developed (Angew. Chem. Int. Ed. 2009, 48, 3333) conditions for the diastereoselective addition of an organometallic to an α-nitrosylated aldehyde, to give, after reduction, the diol 6. Xiaoyu Wu of Shanghai University and Gang Zhao of the Shanghai Institute of Organic Chemistry designed (Adv. Synth. Cat. 2009, 351, 158) an organocatalyst that mediated the enantioselective addition of hydroxyacetone 7 to a range of aldehydes. Andrew G. Myers of Harvard University found (J. Am. Chem. Soc. 2009, 131, 5763) that trialkylaluminum reagents opened epoxides of enol ethers at the more substituted position, delivering protected diols such as 10. Keiji Maruoka of Kyoto University created (Angew. Chem. Int. Ed. 2009, 48, 1838) an organocatalyst for the addition of an aldehyde 11 to an imine 12, to give 13. Markus Kalesse of Leibnitz Universität Hannover showed (Tetrahedron Lett. 2009, 50, 3485) that an organocatalyst could mediate the selective γ-reactivity of 15, leading to 16. Barry M. Trost of Stanford University found (J. Am. Chem. Soc. 2009, 131, 1674) that an organocatalyst directed the addition of diazoacetate 18 to an aldehyde, to give, after further reaction with a trialkylborane, the syn aldol product 19. Professor Trost also demonstrated (J. Am. Chem. Soc. 2009, 131, 4572) that a related complex mediated the conjugate addition of 22 to 21. Enantioselective construction of arrays of alkylated stereogenic centers is a particular challenge. Ji Zhang, then at Pfizer, found (Tetrahedron Lett. 2009, 50, 1167) that the chiral auxiliary of 24 directed both the conjugate addition and the subsequent protonation, and also allowed the product 25 to be brought to > 98% purity by crystallization. Tönis Kanger of Tallinn University of Technology developed (J. Org. Chem. 2009, 74, 3772) an organocatalyst for the conjugate addition of aldehydes to nitrostyrenes such as 26 to give 27.

Carbon-Carbon Bond Formation

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Alkyl Halide ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Phenyl Isocyanate ◽  
Ni Catalyst ◽  
Reductive Coupling ◽  
Carbon Carbon Bond ◽  
University Of Technology ◽  
Osaka Prefecture ◽  
The University

Akiya Ogawa of Osaka Prefecture University found (Tetrahedron Lett. 2010, 51, 6580) that the Sm-mediated reductive coupling of a halide 1 with CO2 to give the carboxylic acid 2 was strongly promoted by visible light. Gregory C. Fu of MIT designed (Angew. Chem. Int. Ed. 2010, 49, 6676) a Ni catalyst for the coupling of a primary borane 4 with a secondary alkyl halide 3. James P. Morken of Boston College devised (Org. Lett. 2010, 12, 3760) conditions for the carbonylative conjugate addition of a dialkyl zinc to an enone 6 to give the 1,4-dicarbonyl product 7. Louis Fensterbank of the Institut Parisien de Chimie Moléculaire developed (Angew. Chem. Int. Ed. 2010, 49, 8721; not illustrated) a protocol for the conjugate addition of alkyl boranes to enones. Hyunik Shin of LG Life Science, Daejeon, and Sang-gi Lee of Ewha Womans University showed (Tetrahedron Lett. 2010, 51, 6893) that the intermediate from Blaise homologation of a nitrile 8 was a powerful nucleophile, smoothly opening an epoxide 10 to deliver 11. Sébastien Reymond and Janine Cossy of ESPCI ParisTech found (J. Org. Chem. 2010, 75, 5151) that FeCl3 smoothly catalyzed the coupling of an alkenyl Grignard 13 with the primary iodide 12. The Ti-mediated coupling of an alkyne 16 with an allylic alkoxide 15 (J. Am. Chem. Soc. 2010, 132, 9576) developed by Glenn C. Micalizio of Scripps/Florida was the key step in the total synthesis (J. Am. Chem. Soc. 2010, 132, 11422) of lehualide B. Huanfeng Jiang of the South China University of Technology observed (Chem. Commun. 2010, 46, 8049) that KI added to a bromoalkyne 18 to give the dihalide 19 with high geometric control. Haruhiko Fuwa of Tohoku University improved (Org. Lett. 2010, 12, 5354) the selective hydroiodination of a methyl alkyne 20 to 21. Takuya Kurahashi and Seijiro Matsubara of Kyoto University devised (Chem. Commun. 2010, 46, 8055) the Ni-catalyzed three-component coupling of an alkyne 22, methyl acrylate 23, and phenyl isocyanate to give the doubly homologated lactam 24. Patrick H. Toy of the University of Hong Kong showed (Synlett 2010, 1997; Org. Lett. 2010, 12, 4996 for a polymer with covalently attached base) that resin-bound triphenylphosphine participated efficiently in the Wittig coupling of 26 with an aldehyde 25.

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