Regio- and stereoselective multisubstituted olefin synthesis via hydro/carboalumination of alkynes and subsequent iron-catalysed cross-coupling reaction with alkyl halides
作者： Shintaro Kawamura , Ryosuke Agata , Masaharu Nakamura
DOI: 10.1039/C5QO00147A
关键词:
摘要: A new synthetic route towards multisubstituted olefins, which are recurring core units in various pharmaceutical and bioactive compounds, was developed based on the direct cross coupling of alkenylaluminium reagents were prepared situ by hydro- carbometalation alkynes, with non-activated alkyl halides presence an iron catalyst. For first time, participated iron-catalysed cross-coupling reaction, following activation aluminium a metal fluoride. The carboalumination alkynes subsequent reactions could be conducted one-pot manner proceeded regio- stereoselectively to give variety di-, tri-, tetrasubstituted alkenes good excellent yields.
rsc.org
sci-hub.se 参考文章(117)
Stefan Bräse, Martin Oestreich, A. de Meijere, Metal-catalyzed cross-coupling reactions and more Wiley-VCH. ,(2014)
憲夫 宮浦, Cross-coupling reactions : a practical guide Springer-Verlag. ,(2002)
D. J. Thompson, K. Smith, Organometallics in synthesis Synthesis. ,vol. 1995, pp. 324- 381 ,(1995) , 10.1039/9781847556134-00324
Ranjan Jana, Tejas P. Pathak, Matthew S. Sigman, Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chemical Reviews. ,vol. 111, pp. 1417- 1492 ,(2011) , 10.1021/CR100327P
G. Natta, G. Allegra, G. Perego, A. Zambelli, A NEW COÖRDINATION TYPE AROUND FLUORINE ATOM Journal of the American Chemical Society. ,vol. 83, pp. 5033- 5033 ,(1961) , 10.1021/JA01485A039
Jun Terao, Misaki Nakamura, Nobuaki Kambe, Non-catalytic conversion of C–F bonds of benzotrifluorides to C–C bonds using organoaluminium reagents Chemical Communications. pp. 6011- 6013 ,(2009) , 10.1039/B915620H
George T. Achonduh, Niloufar Hadei, Cory Valente, Stephanie Avola, Christopher J. O'Brien, Michael G. Organ, On the role of additives in alkyl–alkyl Negishi cross-couplings Chemical Communications. ,vol. 46, pp. 4109- 4111 ,(2010) , 10.1039/C002759F
Ei-ichi Negishi, Zhihong Huang, Guangwei Wang, Swathi Mohan, Chao Wang, Hatsuhiko Hattori, Recent advances in efficient and selective synthesis of di-, tri-, and tetrasubstituted alkenes via Pd-catalyzed alkenylation-carbonyl olefination synergy. Accounts of Chemical Research. ,vol. 41, pp. 1474- 1485 ,(2008) , 10.1021/AR800038E
Gerald Bauer, Matthew D. Wodrich, Rosario Scopelliti, Xile Hu, Iron Pincer Complexes as Catalysts and Intermediates in Alkyl–Aryl Kumada Coupling Reactions Organometallics. ,vol. 34, pp. 289- 298 ,(2015) , 10.1021/OM501122P
Saiko Morooka, Chihiro Wakai, Nobuyuki Matubayasi, Masaru Nakahara, Acid-catalyzed hydrothermal formation of carbon-carbon bond in glycolic acid from a series of formaldehyde producers Chemistry Letters. ,vol. 33, pp. 624- 625 ,(2004) , 10.1246/CL.2004.624