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Carbonylation of Csp3−H Bonds through Oxidative Wittig‐Type Reaction: An Unprecedented Version of Wittig Reaction

dc.contributor.authorZhu, Yingzu
dc.contributor.authorLü, Shiwei
dc.contributor.authorMa, Xingge
dc.contributor.authorZhang, Liang
dc.contributor.authorLuo, Liangliang
dc.contributor.authorJia, Xiaodong
dc.date.accessioned2017-06-16T20:12:57Z
dc.date.available2017-06-16T20:12:57Z
dc.date.issued2016-05
dc.identifier.citationZhu, Yingzu; Lü, Shiwei ; Ma, Xingge; Zhang, Liang; Luo, Liangliang; Jia, Xiaodong (2016). "Carbonylation of Csp3−H Bonds through Oxidative Wittig‐Type Reaction: An Unprecedented Version of Wittig Reaction." Asian Journal of Organic Chemistry 5(5): 617-620.
dc.identifier.issn2193-5807
dc.identifier.issn2193-5815
dc.identifier.urihttps://hdl.handle.net/2027.42/137437
dc.description.abstractA Wittig‐type reaction was achieved by radical cation salt induced aerobic oxidation of Csp3−H bonds. Different from the “standard” version of the Wittig reaction, in which a carbon‐carbon double bond is formed from a carbonyl, carbonyl groups can be installed by similar process.Not from carbonyls but to carbonyls: A Wittig‐type reaction was achieved by radical cation salt induced aerobic oxidation of sp3 C−H bonds. Different from the “standard” version of the Wittig reaction, in which a carbon‐carbon double bond is formed from a carbonyl, carbonyl groups can be installed by similar process.
dc.publisherOxford University Press
dc.publisherWiley Periodicals, Inc.
dc.subject.otherα-anilino phosphonates
dc.subject.otherC−H functionalization
dc.subject.othercarbonylation
dc.subject.otherradical cations
dc.subject.otheroxidative Wittig reaction
dc.titleCarbonylation of Csp3−H Bonds through Oxidative Wittig‐Type Reaction: An Unprecedented Version of Wittig Reaction
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelOrganic Chemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137437/1/ajoc201600055-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137437/2/ajoc201600055.pdf
dc.identifier.doi10.1002/ajoc.201600055
dc.identifier.sourceAsian Journal of Organic Chemistry
dc.identifier.citedreferenceFor selected examples of C−H activation mediated by radical intermediates, see:
dc.identifier.citedreferenceU. S. Dakarapu, A. Bokka, P. Asgari, G. Trog, Y. Hua, H. H. Nguyen, N. Rahman, J. Jeon, Org. Lett. 2015, 17, 5792;
dc.identifier.citedreferenceJ. S. Yu, D. F. Wiemer, J. Org. Chem. 2007, 72, 6263;
dc.identifier.citedreferenceT. Umezawa, T. Seino, F. Matsuda, Org. Lett. 2012, 14, 4206;
dc.identifier.citedreferenceA. Albrecht, F. Morana, A. Fraile, K. A. Jørgensen, Chem. Eur. J. 2012, 18, 10348;
dc.identifier.citedreferenceS. Opekar, R. Pohl, P. Beran, L. Rulíšek, P. Beier, Chem. Eur. J. 2014, 20, 1453;
dc.identifier.citedreferenceJ. Sun, V. A. Keller, S. T. Meyer, S. A. Kozmin, Adv. Synth. Catal. 2010, 352, 839;
dc.identifier.citedreferenceF. P. Touchard, Eur. J. Org. Chem. 2005, 1790;
dc.identifier.citedreferenceS. M. Date, S. K. Ghosh, Angew. Chem. 2007, 119, 390.
dc.identifier.citedreferenceZ. Li, F. Fan, J. Yang, Z.-Q. Liu, Org. Lett. 2014, 16, 3396;
dc.identifier.citedreferenceZ. Li, Y. Zhang, L. Zhang, Z.-Q. Liu, Org. Lett. 2014, 16, 382;
dc.identifier.citedreferenceZ.-Q. Liu, L. Sun, J.-G. Wang, J. Han, Y.-K. Zhao, B. Zhou, Org. Lett. 2009, 11, 1437;
dc.identifier.citedreferenceZ. Li, Y. Xiao, Z.-Q. Liu, Chem. Commun. 2015, 51, 9969;
dc.identifier.citedreferenceK. Chen, J. M. Richter, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 7247;
dc.identifier.citedreferenceT. Yoshimitsu, Y. Arano, H. Nagaoka, J. Am. Chem. Soc. 2005, 127, 11610;
dc.identifier.citedreferenceY. Meng, L.-N. Guo, H. Wang, X.-H. Duan, Chem. Commun. 2013, 49, 7540;
dc.identifier.citedreferenceL. Wang, W. Sha, Q. Dai, X. Feng, W. Wu, H. Peng, B. Chen, J. Cheng, Org. Lett. 2014, 16, 2088;
dc.identifier.citedreferenceD. Liu, C. Liu, H. Li, A. Lei, Chem. Commun. 2014, 50, 3623;
dc.identifier.citedreferenceB. Han, C. Wang, R.-F. Han, W. Yu, X.-Y. Duan, R. Fang, X.-L. Yang, Chem. Commun. 2011, 47, 7818.
dc.identifier.citedreference 
dc.identifier.citedreferenceX.-D. Jia, F.-F. Peng, C. Qing, C.-D. Huo, X.-C. Wang, Org. Lett. 2012, 14, 4030;
dc.identifier.citedreferenceX.-D. Jia, Y.-X. Wang, F.-F. Peng, C.-D. Huo, L.-L. Yu, X.-C. Wang, J. Org. Chem. 2013, 78, 9450;
dc.identifier.citedreferenceY.-X. Wang, F.-F. Peng, J. Liu, C.-D. Huo, X.-C. Wang, X.-D. Jia, J. Org. Chem.; 2015, 80, 609;
dc.identifier.citedreferenceX.-D. Jia, Y.-X. Wang, F.-F. Peng, C.-D. Huo, L.-L. Yu, J. Liu, X.-C. Wang, Adv. Synth. Catal. 2014, 356, 1210;
dc.identifier.citedreferenceJ. Liu, F. Liu, Y.-Z. Zhu, X.-G. Ma, X.-D. Jia, Org. Lett. 2015, 17, 1409.
dc.identifier.citedreferenceG. Wittig, G. Geissler, Liebigs Ann. Chem. 1953, 580, 44.
dc.identifier.citedreferenceFor selected reviews, see:
dc.identifier.citedreferenceB. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863;
dc.identifier.citedreferenceH.-J. Cristau, Chem. Rev. 1994, 94, 1299;
dc.identifier.citedreferenceT. Rein, T. M. Pederson, Synthesis 2002, 5, 579;
dc.identifier.citedreferenceR. W. Hoffmann, Angew. Chem. Int. Ed. 2001, 40, 1411; Angew. Chem. 2001, 113, 1457;
dc.identifier.citedreferenceN. J. Lawrence in Preparation of Alkenes: A Practical Approach (Ed.: J. M. J. Williams ), Oxford University Press, Oxford, 1995;
dc.identifier.citedreferenceO. I. Kolodiazhnyi, Phosphorus Ylides: Chemistry and Applications in Organic Chemistry, Wiley-VCH, New York, 1999.
dc.identifier.citedreferenceFor Wittig reactions, see:
dc.identifier.citedreferenceW. A. Herrmann, M. Wang, Angew. Chem. Int. Ed. Engl. 1991, 30, 1641; Angew. Chem. 1991, 103, 1709;
dc.identifier.citedreferenceH. Lebel, V. Paquet, C. Proulx, Angew. Chem. Int. Ed. 2001, 40, 2887; Angew. Chem. 2001, 113, 2971;
dc.identifier.citedreferenceG. A. Mirafzal, G. Cheng, L. K. Woo, J. Am. Chem. Soc. 2002, 124, 176;
dc.identifier.citedreferenceA. M. Santos, C. C. Romao, F. E. Kuhn, J. Am. Chem. Soc. 2003, 125, 2414;
dc.identifier.citedreferenceV. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. de Vincente, J. Am. Chem. Soc. 2003, 125, 6034;
dc.identifier.citedreferenceY. Chen, L. Huang, X. P. Zhang, J. Org. Chem. 2003, 68, 5925;
dc.identifier.citedreferenceY. Chen, L. Huang, X. P. Zhang, Org. Lett. 2003, 5, 2493;
dc.identifier.citedreferenceC. Huo, X. He, T. H. Chan, J. Org. Chem. 2008, 73, 8583.
dc.identifier.citedreferenceFor Staudinger reactions, see:
dc.identifier.citedreferenceI. Freifeld, H. Shojaei, P. Langer, J. Org. Chem. 2006, 71, 4965;
dc.identifier.citedreferenceS. P. Marsden, A. E. McGonagle, B. McKeever-Abbas, Org. Lett. 2008, 10, 2589;
dc.identifier.citedreferenceN. Y. Huang, M. G. Liu, M. W. Ding, J. Org. Chem. 2009, 74, 6874;
dc.identifier.citedreferenceA. Ramazani, A. Rezaei, Org. Lett. 2010, 12, 2852;
dc.identifier.citedreferenceY. B. Nie, L. Wang, M. W. Ding, J. Org. Chem. 2012, 77, 696;
dc.identifier.citedreferenceH. Xie, D. Yuan, M. W. Ding, J. Org. Chem. 2012, 77, 2954;
dc.identifier.citedreferenceO. A. Attanasi, S. Bartoccini, G. Favi, P. Filippone, F. R. Perrulli, S. Santeusanio, J. Org. Chem. 2012, 77, 9338;
dc.identifier.citedreferenceR. Kumar, D. S. Ermolat′ev, E. V. Van der Eycken, J. Org. Chem. 2013, 78, 5737.
dc.identifier.citedreferenceFor selected examples of HWE olefination, see:
dc.identifier.citedreferenceG. A. Molander, R. Figueroa, J. Org. Chem. 2006, 71, 6135;
dc.identifier.citedreferenceV. D. Pinho, A. C. B. Burtoloso, J. Org. Chem. 2011, 76, 289;
dc.identifier.citedreferenceL. Franchini, F. Compostella, D. Colombo, L. Panza, F. Ronchetti, J. Org. Chem. 2010, 75, 5363;
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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