One-pot synthesis of trisubstituted conjugated dienes via sequential Suzuki-Miyaura cross-coupling with alkenyl- and alkyltrifluoroborates

The Journal of Organic Chemistry
Gary A Molander, Yasuo Yokoyama

Abstract

The sequential, stereoselective disubstitution of 1,1-dibromoalkenes using a variety of alkenyltrifluoroborates followed by alkyltrifluoroborates in the presence of Pd(PPh3)4 is described. This synthetic method proceeds smoothly in one pot under mild reaction conditions to provide the corresponding trisubstituted, conjugated dienes in excellent yield. Moreover, the method is operationally very simple because the organotrifluoroborates are stable in air, and the byproducts are innocuous inorganic salts.

References

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Jun 13, 2002·Journal of the American Chemical Society·Karl A ScheidtWilliam R Roush
Nov 6, 2003·Journal of the American Chemical Society·Xingzhong ZengEi-ichi Negishi
May 7, 2005·The Journal of Organic Chemistry·Gary A Molander, Luciana A Felix
Jun 9, 2005·Journal of the American Chemical Society·Hongmei Li, Patrick J Walsh
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Oct 14, 2005·Journal of the American Chemical Society·Gary A Molander, María Ribagorda
Dec 3, 2005·Organic Letters·Takeshi ShimizuMikiko Sodeoka

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Citations

Nov 17, 2011·Chemical Reviews·Giorgio Chelucci
Sep 9, 2006·The Journal of Organic Chemistry·Gary A Molander, Noel M Ellis
Aug 27, 2009·Chemical Communications : Chem Comm·Stephen G NewmanMark Lautens
Jul 8, 2015·The Journal of Organic Chemistry·Gary A Molander
May 17, 2011·Angewandte Chemie·Ian T CrouchDoug E Frantz
Apr 13, 2012·Chemical Communications : Chem Comm·Shengqing YeJie Wu
Oct 5, 2013·Chemical Society Reviews·Alastair J J Lennox, Guy C Lloyd-Jones
Feb 1, 2011·Chemistry : a European Journal·Juan Marco-MartínezDiego J Cárdenas
Jan 28, 2017·Monatshefte für chemie·Patrick DobrounigRolf Breinbauer
Aug 16, 2008·The Journal of Organic Chemistry·Jinlong ZhaoKai Cheng
Sep 26, 2009·Organic Letters·Virtudes Pardo-RodríguezDiego J Cárdenas
Jul 23, 2008·Organic Letters·Juan Marco-MartínezDiego J Cárdenas
Dec 22, 2007·Chemical Reviews·Sylvain Darses, Jean-Pierre Genet

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