Barbier-Negishi Coupling of Secondary Alkyl Bromides with Aryl and Alkenyl Triflates and Nonaflates

Angewandte Chemie
Ke-Feng ZhangOlivier Baudoin

Abstract

A mild and practical Barbier-Negishi coupling of secondary alkyl bromides with aryl and alkenyl triflates and nonaflates has been developed. This challenging reaction was enabled by the use of a very bulky imidazole-based phosphine ligand, which resulted in good yields as well as good chemo- and site selectivities for a broad range of substrates at room temperature and under non-aqueous conditions. This reaction was extended to primary alkyl bromides by using an analogous pyrazole-based ligand.

References

Oct 25, 2001·The Journal of Organic Chemistry·Mario Rottländer, Paul Knochel
Jan 23, 2004·Chemical Communications : Chem Comm·Alexander ZapfMatthias Beller
Jun 24, 2004·Chemistry : a European Journal·Franck RataboulMatthias Beller
Oct 8, 2004·Journal of the American Chemical Society·Jacqueline E Milne, Stephen L Buchwald
May 16, 2009·Journal of the American Chemical Society·Chong Han, Stephen L Buchwald
Oct 16, 2009·Journal of the American Chemical Society·Arkady KrasovskiyBruce H Lipshutz
Jan 12, 2010·Chemical Communications : Chem Comm·Christophe DuplaisBruce H Lipshutz
Apr 10, 2010·Chemical Communications : Chem Comm·Tobias D BlümkePaul Knochel
Feb 3, 2011·Chemical Communications : Chem Comm·Selçuk Çalimsiz, Michael G Organ
Feb 8, 2014·Angewandte Chemie·Anthony MilletOlivier Baudoin
Aug 19, 2015·Nature·Laura K G AckermanDaniel J Weix
Oct 27, 2016·Angewandte Chemie·Stéphanie DupuyOlivier Baudoin

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