Unprecedented negishi coupling at C-br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis

The Journal of Organic Chemistry
Yulia A Getmanenko, Robert J Twieg

Abstract

The 2-bromo-5(or 6)-tri-n-butylstannylpyridines, prepared from dibromopyridines and i-PrMgCl at room temperature, undergo Negishi coupling with either alkyl or arylzinc chlorides. The new alkyl- and aryl-substituted pyridylstannanes produced are shown to be suitable for further functionalization by Stille coupling. A group of new liquid crystalline materials with aromatic cores comprised of pyridine and thiophene rings were prepared utilizing these new pyridinylstannanes as key intermediates.

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Citations

Mar 25, 2011·Macromolecular Rapid Communications·Xiaolian HuHongzheng Chen
Feb 4, 2011·Angewandte Chemie·Teruhisa TsuchimotoHiroshi Takahashi
Jun 9, 2016·The Journal of Organic Chemistry·Toru HashimotoRyo Takeuchi
Jul 14, 2012·The Journal of Organic Chemistry·Jason J HanthornDerek A Pratt
Mar 28, 2017·Chemical Communications : Chem Comm·Sébastien LaulhéJennifer L Roizen
Nov 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Seung-Hoi Kim, Reuben D Rieke
Jan 7, 2016·Beilstein Journal of Organic Chemistry·Bijay Shrestha, Ramesh Giri

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