Organic Chemistry

Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

Authors

  • Jian-Fei Bai School of Biological and Chemical Engineering, NingboTech University ,
  • Jianbo Tang College of Chemistry and Chemical Engineering, Lanzhou University ,
  • Xiaolong Gao Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences ,
  • Zhi-Jiang Jiang School of Biological and Chemical Engineering, NingboTech University ,
  • Jia Chen School of Biological and Chemical Engineering, NingboTech University ,
  • Zhanghua Gao School of Biological and Chemical Engineering, NingboTech University

Abstract

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

Version notes

correct errors, co-author added

Content

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Supplementary material

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Supporting Information
Including the general information, synthesis of substrates, reference, crystallographic data and NMR spectra
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XRD of 3p
XRD