One-Pot Sonogashira Coupling–Cyclization toward Regioselective Synthesis of Benzosultams

A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes is presented. This method allows access to a variety of substituted benzosultams regioselectively in excellent yields. The reasons for regioselectivity are interpreted through density fun...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-04, Vol.80 (8), p.3940-3948
Main Authors: Debnath, Sudarshan, Mondal, Shovan
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Benzene Derivatives - chemistry
Catalysis
Cyclization
Molecular Structure
Quantum Theory
Stereoisomerism
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
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Summary:A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes is presented. This method allows access to a variety of substituted benzosultams regioselectively in excellent yields. The reasons for regioselectivity are interpreted through density functional theory (DFT) studies.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00274