Direct 2-Pyridyl-Alkylation of Benzyne with N-Alkylpyridinium Salts

Author:

Xia Ji-Bao1ORCID,Su Yijin1,Guo Ning-Xin12

Affiliation:

1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences

2. University of Chinese Academy of Sciences

Abstract

AbstractA 2-pyridyl-alkylation of benzyne using N-alkylpyridinium salts has been developed under either photochemical or thermal conditions. This metal-free dicarbofunctionalization of benzyne undergoes a de Mayo-type process including cascade dearomative [3+2] cycloaddition and rearomative ring-opening reaction. An electron-deficient N-cyclic alkyl group was necessary. A formal ortho-C–H arylation of pyridine has been achieved.

Funder

National Natural Science Foundation of China

Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences

State Key Laboratory for Oxo Synthesis and Selective Oxidation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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