Fe(ii)-Catalyzed azidation of polybutadienes using the Zhdankin reagent

2019 ◽  
Vol 10 (39) ◽  
pp. 5348-5352
Author(s):  
Haeji Jung ◽  
Yeong-Gweon Lim

Phenyl-terminated polybutadienes (PtPBs) are efficiently converted to azidated PtPBs using the Zhdankin reagent generated in situ from iodosobenzoic acid and TMSN3 with an iron catalyst.


2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).



Author(s):  
Douglass F. Taber

The catalytic reduction of the alkene 1 gave the cis-fused product (not illustrated), by kinetic H₂ addition to the less congested face of the alkene. Ryan A. Shenvi of Scripps La Jolla found (J. Am. Chem. Soc. 2014, 136, 1300) conditions for stepwise HAT, con­verting 1 to the thermodynamically-favored trans-fused ketone 2. Seth B. Herzon of Yale University devised (J. Am. Chem. Soc. 2014, 136, 6884) a protocol for the reduc­tion, mediated by 4, of the double bond of a haloalkene 3 to give the saturated halide 5. The Shenvi conditions also reduced a haloalkene to the saturated halide. Daniel J. Weix of the University of Rochester and Patrick L. Holland, also of Yale University, established (J. Am. Chem. Soc. 2014, 136, 945) conditions for the kinetic isomerization of a terminal alkene 6 to the Z internal alkene 7. Christoforos G. Kokotos of the University of Athens showed (J. Org. Chem. 2014, 79, 4270) that the ketone 9, used catalytically, markedly accelerated the Payne epoxidation of 8 to 10. Note that Helena M. C. Ferraz of the Universidade of São Paulo reported (Tetrahedron Lett. 2000, 41, 5021) several years ago that alkene epoxidation was also easily carried out with DMDO generated in situ from acetone and oxone. Theodore A. Betley of Harvard University prepared (Chem. Sci. 2014, 5, 1526) the allylic amine 12 by reacting the alkene 11 with 1-azidoadamantane in the presence of an iron catalyst. Rodney A. Fernandes of the Indian Institute of Technology Bombay developed (J. Org. Chem. 2014, 79, 5787) efficient conditions for the Wacker oxida­tion of a terminal alkene 6 to the methyl ketone 13. Yong-Qiang Wang of Northwest University oxidized (Org. Lett. 2014, 16, 1610) the alkene 6 to the enone 14. Peili Teo of the National University of Singapore devised (Chem. Commun. 2014, 50, 2608) conditions for the Markovnikov hydration of the alkene 6 to the alcohol 15. Internal alkenes were inert under these conditions, but Yoshikazo Kitano of the Tokyo University of Agriculture and Technology effected (Synthesis 2014, 46, 1455) the Markovnikov amination (not illustrated) of more highly substituted alkenes.



Author(s):  
Douglass F. Taber

Daniel J. Weix of the University of Rochester effected (Org. Lett. 2012, 14, 1476) the in situ reductive coupling of an alkyl halide 2 with an acid chloride 1 to deliver the ketone 3. André B. Charette of the Université de Montréal (not illustrated) developed (Nature Chem. 2012, 4, 228) an alternative route to ketones by the coupling of an organometallic with an in situ-activated secondary amide. Mahbub Alam and Christopher Wise of the Merck, Sharpe and Dohme UK chemical process group optimized (Org. Process Res. Dev. 2012, 16, 453) the opening of an epoxide 4 with a Grignard reagent 5. Ling Song of the Fujian Institute of Research on the Structure of Matter optimized (J. Org. Chem. 2012, 77, 4645) conditions for the 1,2-addition of a Grignard reagent (not illustrated) to a readily enolizable ketone. Wei-Wei Liao of Jilin University conceived (Org. Lett. 2012, 14, 2354) of an elegant assembly of highly functionalized quaternary centers, as illustrated by the conversion of 7 to 8. Antonio Rosales of the University of Granada and Ignacio Rodríguez-García of the University of Almería prepared (J. Org. Chem. 2012, 77, 4171) free radicals by reduction of an ozonide 9 in the presence of catalytic titanocene dichloride. In the absence of the acceptor 10, the dimer of the radical was obtained, presenting a simple alternative to the classic Kolbe coupling. Marc L. Snapper of Boston College found (Eur. J. Org. Chem. 2012, 2308) that the difficult ketone 12 could be methylenated following a modified Peterson protocol. Yoshito Kishi of Harvard University optimized (Org. Lett. 2012, 14, 86) the coupling of 15 with 16 to give 17. Masaharu Nakamura of Kyoto University devised (J. Org. Chem. 2012, 77, 1168) an iron catalyst for the coupling of 18 with 19. The specific preparation of trisubsituted alkenes is an ongoing challenge. Quanri Wang of Fudan University and Andreas Goeke of Givaudan Shanghai fragmented (Angew. Chem. Int. Ed. 2012, 51, 5647) the ketone 21 by exposure to 22 to give the macrolide 23 with high stereocontrol.





2017 ◽  
Vol 19 (10) ◽  
pp. 2356-2360 ◽  
Author(s):  
Alonso Rosas-Hernández ◽  
Christoph Steinlechner ◽  
Henrik Junge ◽  
Matthias Beller

A highly selective earth-abundant photocalytic system, based on an in situ copper photosensitizer and an iron catalyst, was developed for the CO2-to-CO transformation.



2015 ◽  
Vol 137 (45) ◽  
pp. 14232-14235 ◽  
Author(s):  
Cesar M. Manna ◽  
Aman Kaur ◽  
Lauren M. Yablon ◽  
Fredrik Haeffner ◽  
Bo Li ◽  
...  


1985 ◽  
Vol 118 (2) ◽  
pp. 156-158 ◽  
Author(s):  
A.V. Bobrov ◽  
Yn.M. Kimel'fel'd ◽  
L.S. Glebov ◽  
G.A. Kliger ◽  
S.M. Loktev
Keyword(s):  


Author(s):  
Douglass F. Taber

Erick M. Carreira of ETH-Zürich generated (Org. Lett. 2012, 14, 2162) ethyl diazoacetate in situ in the presence of the alkene 1 and an iron catalyst to give the cyclopropane 3. Joseph M. Fox of the University of Delaware inserted (Chem. Sci. 2012, 3, 1589) the Rh carbene derived from 5 into the alkene 4 to give the cyclopropene 6, without β-hydride elimination. Masaatsu Adachi and Toshio Nishikawa of Nagoya University reduced (Chem. Lett. 2012, 41, 287) the enone 7 to give the cyclobutanol 8. Intramolecular ketene cycloaddition has been limited to very electron-rich acceptor alkenes. Xiao-Ping Cao and Yong-Qiang Tu of Lanzhou University devised (Chem. Sci. 2012, 3, 1975) a protocol that converted 9 into the cyclobutanone 10 with high diastereocontrol. The intermediate is the tosylhydrazone of the ketone, so a reductive workup would lead to the corresponding cycloalkane. Koichi Mikami of the Tokyo Institute of Technology added (J. Am. Chem. Soc. 2012, 134, 10329) alkyl cuprates to the prochiral enone 11 to give the enolate trapping product 13 in high ee and with high diastereocontrol. Marcus A. Tius of the University of Hawaii found (Angew. Chem. Int. Ed. 2012, 51, 5727) a Pd catalyst for the Nazarov cyclization of 14 to 15. Antoni Riera and Xavier Verdaguer of the Universitat de Barcelona prepared (Org. Lett. 2012, 14, 3534) 16 by enantioselective Pauson-Khand addition to tetramethyl norbornadiene. Conjugate addition followed by retro Diels-Alder could potentially lead to the cyclopentenone 17. The intermolecular Pauson-Khand cyclization often gives mixtures of regioisomers. José Barluenga of the Universidad de Oviedo demonstrated (Angew. Chem. Int. Ed. 2012, 51, 183) an alternative, the addition of an alkenyl lithium 19 to the Fischer carbene 18 leading to 20. Jian-Hua Xie and Qi-Lin Zhou of Nankai University hydrogenated (Adv. Synth. Catal. 2012, 354, 1105; see also Org. Lett. 2012, 14, 2714) the ketone 21 under epimerizing conditions to give the alcohol 22. Kozo Shishido of the University of Tokushima observed (Tetrahedron Lett. 2012, 53, 145) that the intramolecular Heck cyclization of 23 proceeded with high diastereocontrol. Zhi-Xiang Yu of Peking University devised (Org. Lett. 2012, 14, 692) an Rh catalyst for the cyclocarbonylation of 25 to 26.



2015 ◽  
Vol 1113 ◽  
pp. 459-464 ◽  
Author(s):  
Nur Hanina Malek ◽  
Mohammad Asadullah ◽  
Arina Sauki

Tar removal from producer gas was investigated using activated carbon supported iron catalyst. Activated carbon was derived from jute stick biomass. The catalyst surface areas and pore volume were characterized by using iodiometric titration which shows that as the iron loading percentage increased, the adsorption capability was also increased which represents the increment of pore volume of the catalyst. Based on XRD pattern, the iron species formed on the activated carbon surface is mostly amorphous magnetite (Fe3O4) species coexisted with the reduced irons (α-Fe and γ-Fe). The reduced iron on catalyst surface justify the active phase which enhances the tar reforming during biomass gasification.



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