Functionalization of Styrenes by Copper‐Catalyzed Borylation/ ortho‐Cyanation and Silver‐Catalyzed Annulation Processes
dc.contributor.author | Zhao, Wanxiang | en_US |
dc.contributor.author | Montgomery, John | en_US |
dc.date.accessioned | 2015-11-12T21:04:02Z | |
dc.date.available | 2016-12-01T14:33:05Z | en |
dc.date.issued | 2015-10-19 | en_US |
dc.identifier.citation | Zhao, Wanxiang; Montgomery, John (2015). "Functionalization of Styrenes by Copper‐Catalyzed Borylation/ ortho‐Cyanation and Silver‐Catalyzed Annulation Processes." Angewandte Chemie International Edition 54(43): 12683-12686. | en_US |
dc.identifier.issn | 1433-7851 | en_US |
dc.identifier.issn | 1521-3773 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/115938 | |
dc.description.abstract | An efficient two‐step method for the assembly of indanone derivatives starting from a simple vinyl arene has been developed. The sequence first involves addition of bis(pinacolato)diboron (B2pin2) and N‐cyano‐N‐phenyl‐p‐methylbenzenesulfonamide (NCTS) to a broad range of styrenes by utilizing IMesCuCl as catalyst. This step simultaneously accomplishes hydroboration of the alkene and ortho cyanation of the benzene unit. The products thus obtained are further functionalized by a AgNO3/Selectfluor‐mediated coupling of the BPin and cyano functionalities to annulate a new five‐membered ring. This combined two‐step sequence provides a versatile method for the site‐selective derivatization of a broad range of vinyl arene substrates.A Cu and Ag sequence: The bis‐functionalization of styrenes is accomplished through a copper‐catalyzed process that enables hydroboration of the alkene and regioselective ortho cyanation of the arene. The resulting adducts are converted, by a radical cyclization process, into a cyclopentanone unit fused to the original aromatic ring. Together, these methods allow efficient cyclopentannulation of a broad range of styrene derivatives. | en_US |
dc.publisher | WILEY‐VCH Verlag | en_US |
dc.subject.other | radicals | en_US |
dc.subject.other | annulations | en_US |
dc.subject.other | silver | en_US |
dc.subject.other | copper | en_US |
dc.subject.other | cyclizations | en_US |
dc.title | Functionalization of Styrenes by Copper‐Catalyzed Borylation/ ortho‐Cyanation and Silver‐Catalyzed Annulation Processes | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109‐1055 (USA) http://www.umich.edu/∼jmgroup | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/115938/1/anie_201507303_sm_miscellaneous_information.pdf | |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/115938/2/12683_ftp.pdf | |
dc.identifier.doi | 10.1002/anie.201507303 | en_US |
dc.identifier.source | Angewandte Chemie International Edition | en_US |
dc.identifier.citedreference | Y.‐C. Wong, K. Parthasarathy, C.‐H. Cheng, Org. Lett. 2010, 12, 1736 – 1739; | en_US |
dc.identifier.citedreference | Y. Yang, S. L. Buchwald, Angew. Chem. Int. Ed. 2014, 53, 8677 – 8681; Angew. Chem. 2014, 126, 8821 – 8825. | en_US |
dc.identifier.citedreference | Y. Yang, P. Liu, ACS Catal. 2015, 5, 2944 – 2951. | en_US |
dc.identifier.citedreference | C. Zhou, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 2302 – 2303; | en_US |
dc.identifier.citedreference | C. Zhou, R. C. Larock, J. Org. Chem. 2006, 71, 3551 – 3558; | en_US |
dc.identifier.citedreference | For other processes involving 1,3‐migrations of styrenyl systems: | en_US |
dc.identifier.citedreference | B. W. Zhao, X. Y. Lu, Tetrahedron Lett. 2006, 47, 6765 – 6768; | en_US |
dc.identifier.citedreference | G. C. Tsui, Q. Glenadel, C. Lau, M. Lautens, Org. Lett. 2011, 13, 208 – 211; | en_US |
dc.identifier.citedreference | K. Ueura, S. Miyamura, T. Satoh, M. Miura, J. Organomet. Chem. 2006, 691, 2821 – 2826; | en_US |
dc.identifier.citedreference | X. Wang, M. Liu, L. Xu, Q. Wang, J. Chen, J. Ding, H. Wu, J. Org. Chem. 2013, 78, 5273 – 5281; | en_US |
dc.identifier.citedreference | X. Y. Wang, X. D. Wang, M. C. Liu, J. C. Ding, J. X. Chen, H. Y. Wu, Synthesis 2013, 2241 – 2244. | en_US |
dc.identifier.citedreference | en_US | |
dc.identifier.citedreference | G. A. Molander, V. Colombel, V. A. Braz, Org. Lett. 2011, 13, 1852 – 1855; | en_US |
dc.identifier.citedreference | J. W. Lockner, D. D. Dixon, R. Risgaard, P. S. Baran, Org. Lett. 2011, 13, 5628 – 5631; | en_US |
dc.identifier.citedreference | G. Sorin, R. Martinez Mallorquin, Y. Contie, A. Baralle, M. Malacria, J.‐P. Goddard, L. Fensterbank, Angew. Chem. Int. Ed. 2010, 49, 8721 – 8723; Angew. Chem. 2010, 122, 8903 – 8905; | en_US |
dc.identifier.citedreference | Y. Yasu, T. Koike, M. Akita, Adv. Synth. Catal. 2012, 354, 3414 – 3420; | en_US |
dc.identifier.citedreference | K. Miyazawa, Y. Yasu, T. Koike, M. Akita, Chem. Commun. 2013, 49, 7249 – 7251; | en_US |
dc.identifier.citedreference | J. C. Tellis, D. N. Primer, G. A. Molander, Science 2014, 345, 433 – 436; | en_US |
dc.identifier.citedreference | D. N. Primer, I. Karakaya, J. C. Tellis, G. A. Molander, J. Am. Chem. Soc. 2015, 137, 2195 – 2198; | en_US |
dc.identifier.citedreference | O. Gutierrez, J. C. Tellis, D. N. Primer, G. A. Molander, M. C. Kozlowski, J. Am. Chem. Soc. 2015, 137, 4896 – 4899. | en_US |
dc.identifier.citedreference | For radical additions of boronic acids: | en_US |
dc.identifier.citedreference | I. B. Seiple, S. Su, R. A. Rodriguez, R. Gianatassio, Y. Fujiwara, A. L. Sobel, P. S. Baran, J. Am. Chem. Soc. 2010, 132, 13194 – 13196; | en_US |
dc.identifier.citedreference | Y. Fujiwara, V. Domingo, I. B. Seiple, R. Gianatassio, M. Del Bel, P. S. Baran, J. Am. Chem. Soc. 2011, 133, 3292 – 3295; | en_US |
dc.identifier.citedreference | For a process with catecholboranes: A. Kapat, A. König, F. Montermini, P. Renaud, J. Am. Chem. Soc. 2011, 133, 13890 – 13893. | en_US |
dc.identifier.citedreference | B. A. Vaughan, M. S. Webster‐Gardiner, T. R. Cundari, T. B. Gunnoe, Science 2015, 348, 421 – 424. | en_US |
dc.identifier.citedreference | en_US | |
dc.identifier.citedreference | M. Tobisu, I. Hyodo, M. Onoe, N. Chatani, Chem. Commun. 2008, 6013 – 6015; | en_US |
dc.identifier.citedreference | For an overview of directed C‐H functionalizations: T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147 – 1169. | en_US |
dc.identifier.citedreference | For annulations involving styrenes: | en_US |
dc.identifier.citedreference | A. R. Sanger, J. Mol. Catal. A 2002, 188, 11 – 16; | en_US |
dc.identifier.citedreference | S. S. Bhojgude, A. Bhunia, R. G. Gonnade, A. T. Biju, Org. Lett. 2014, 16, 676 – 679. | en_US |
dc.identifier.citedreference | For other types of annulations: | en_US |
dc.identifier.citedreference | H. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248 – 3249; | en_US |
dc.identifier.citedreference | P. C. Montevecchi, M. L. Navacchia, P. Spagnolo, Tetrahedron 1998, 54, 8207 – 8216; | en_US |
dc.identifier.citedreference | R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604 – 1606; | en_US |
dc.identifier.citedreference | R. L. Danheiser, R. G. Brisbois, J. J. Kowalczyk, R. F. Miller, J. Am. Chem. Soc. 1990, 112, 3093 – 3100; | en_US |
dc.identifier.citedreference | G. H. Posner, Chem. Rev. 1986, 86, 831 – 844; | en_US |
dc.identifier.citedreference | R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem. 1998, 63, 7652 – 7662; | en_US |
dc.identifier.citedreference | E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578 – 9579; | en_US |
dc.identifier.citedreference | L. Ackermann, Acc. Chem. Res. 2014, 47, 281 – 295. | en_US |
dc.identifier.citedreference | R. D. Grigg, R. van Hoveln, J. M. Schomaker, J. Am. Chem. Soc. 2012, 134, 16131 – 16134; | en_US |
dc.identifier.citedreference | J. M. Schomaker, R. D. Grigg, Synlett 2013, 401 – 407; | en_US |
dc.identifier.citedreference | R. J. Van Hoveln, S. C. Schmid, J. M. Schomaker, Org. Biomol. Chem. 2014, 12, 7655 – 7658; | en_US |
dc.identifier.citedreference | R. J. Van Hoveln, S. C. Schmid, M. Tretbar, C. T. Buttke, J. M. Schomaker, Chem. Sci. 2014, 5, 4763 – 4767; | en_US |
dc.identifier.citedreference | R. Van Hoveln, B. M. Hudson, H. B. Wedler, D. M. Bates, G. Le Gros, D. J. Tantillo, J. M. Schomaker, J. Am. Chem. Soc. 2015, 137, 5346 – 5354. | en_US |
dc.identifier.citedreference | For representative copper‐catalyzed processes involving BPin: | en_US |
dc.identifier.citedreference | R. Corberán, N. W. Mszar, A. H. Hoveyda, Angew. Chem. Int. Ed. 2011, 50, 7079 – 7082; Angew. Chem. 2011, 123, 7217 – 7220; | en_US |
dc.identifier.citedreference | H. Jang, A. R. Zhugralin, Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 7859 – 7871; | en_US |
dc.identifier.citedreference | R. Sakae, K. Hirano, M. Miura, J. Am. Chem. Soc. 2015, 137, 6460 – 6463; | en_US |
dc.identifier.citedreference | J. H. Moon, H.‐Y. Jung, Y. J. Lee, S. W. Lee, J. Yun, J. Y. Lee, Organometallics 2015, 34, 2151 – 2159; | en_US |
dc.identifier.citedreference | For recent illustrations with other metals: S. N. Mlynarski, C. H. Schuster, J. P. Morken, Nature 2014, 505, 386 – 390. | en_US |
dc.identifier.citedreference | For representative catalytic processes involving Ph(Ts)N‐CN: | en_US |
dc.identifier.citedreference | P. Anbarasan, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2011, 50, 519 – 522; Angew. Chem. 2011, 123, 539 – 542; | en_US |
dc.identifier.citedreference | Y. Yang, Y. Zhang, J. Wang, Org. Lett. 2011, 13, 5608 – 5611; | en_US |
dc.identifier.citedreference | P. Anbarasan, H. Neumann, M. Beller, Chem. Eur. J. 2011, 17, 4217 – 4222; | en_US |
dc.identifier.citedreference | T.‐J. Gong, B. Xiao, W.‐M. Cheng, W. Su, J. Xu, Z.‐J. Liu, L. Liu, Y. Fu, J. Am. Chem. Soc. 2013, 135, 10630 – 10633; | en_US |
dc.identifier.citedreference | M. Chaitanya, D. Yadagiri, P. Anbarasan, Org. Lett. 2013, 15, 4960 – 4963; | en_US |
dc.identifier.citedreference | D. G. Yu, T. Gensch, F. de Azambuja, S. Vasquez‐Cespedes, F. Glorius, J. Am. Chem. Soc. 2014, 136, 17722 – 17725; | en_US |
dc.identifier.citedreference | W. P. Liu, L. Ackermann, Chem. Commun. 2014, 50, 1878 – 1881; | en_US |
dc.identifier.citedreference | J. Han, C. D. Pan, X. F. Jia, C. J. Zhu, Org. Biomol. Chem. 2014, 12, 8603 – 8606; | en_US |
dc.identifier.citedreference | J. Li, L. Ackermann, Angew. Chem. Int. Ed. 2015, 54, 3635 – 3638; Angew. Chem. 2015, 127, 3706 – 3709. | en_US |
dc.identifier.citedreference | D. S. Laitar, E. Y. Tsui, J. P. Sadighi, Organometallics 2006, 25, 2405 – 2408. | en_US |
dc.identifier.citedreference | en_US | |
dc.identifier.citedreference | Z. Li, Z. Wang, L. Zhu, X. Tan, C. Li, J. Am. Chem. Soc. 2014, 136, 16439 – 16443; | en_US |
dc.identifier.citedreference | F. Yin, Z. Wang, Z. Li, C. Li, J. Am. Chem. Soc. 2012, 134, 10401 – 10404; | en_US |
dc.identifier.citedreference | Z. Li, L. Song, C. Li, J. Am. Chem. Soc. 2013, 135, 4640 – 4643; | en_US |
dc.identifier.citedreference | C. Zhang, Z. Li, L. Zhu, L. Yu, Z. Wang, C. Li, J. Am. Chem. Soc. 2013, 135, 14082 – 14085; L. Zhu, H. Chen, Z. Wang, C. Li, Org. Chem. Front. 2014, 1, 1299 – 1305. | en_US |
dc.identifier.citedreference | C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415 – 3434. | en_US |
dc.identifier.citedreference | en_US | |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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