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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper-catalyzed enantioselective arylalkynylation of alkenes
Guangyue Lei1, Hanwen Zhang1, Bin Chen1
1State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry , Center for Excellence in Molecular Synthesis , University of Chinese Academy of Sciences , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , P. R. China .
Abstract:
A copper-catalyzed enantioselective arylalkynylation of alkenes with diaryliodonium salt and a monosubstituted alkyne is reported. The three-component coupling reactions proceed under mild reaction conditions with a broad substrate scope, leading to synthetically valuable 1,2-diaryl-3-butynes. The key to the success of this chemistry is the employment of the chiral bisoxazoline-phenylaniline (BOPA) ligand. A novel reaction pathway involving the phenyl radical generation under thermal copper catalysis is proposed according to mechanistic studies.
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