Broadly Applicable Ion Pair-Assisted Nucleophilic Substitution of sp³-Carbon Electrophiles with Alkynyltrifluoroborates

Shiwen Liu, Cláudio F. Tormena, Gerald B. Hammond* and Bo Xu*

*University of Louisville. Louisville, Kentucky 40292, United States; Donghua University, Shanghai 201620, China, Email: gb.hammondlouisville.edu, bo.xudhu.edu.cn

S. Liu, C. F. Tormena, G. B. Hammond, B. Xu, Org. Lett., 2022, 24, 6298-6303.

DOI: 10.1021/acs.orglett.2c02507

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Abstract

Alkynyltrifluoroborate nucleophiles react smoothly with a wide range of sp³-carbon electrophiles, including propargyl methanesulfonates and unactivated alkyl triflates, to give Sonogashira-type products via a novel ion pair-assisted nucleophilic substitution mechanism.

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proposed mechanism

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Key Words

alkynylation

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ID: J54-Y2022