From Difluoromethyl 2-Pyridyl Sulfone to Difluorinated Sulfonates: A Protocol for Nucleophilic Difluoro(sulfonato)methylation

An efficient method for the synthesis of alkyl α,α‐difluorosulfonates has been developed. The selection of the 2‐pyridyl group as the aryl substitute on the sulfone is critically important for the success of this transformation (see scheme). The synthetic application of fluorinated sulfones is exten...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2011-03, Vol.50 (11), p.2559-2563
Main Authors: Prakash, G.K. Surya, Ni, Chuanfa, Wang, Fang, Hu, Jinbo, Olah, George A
Format: Article
Language:English
Subjects:
Alkanesulfonates - chemical synthesis
Alkanesulfonates - chemistry
fluorine
Fluorine - chemistry
ipso-substitution
Methylation
Molecular Structure
nucleophilic fluoroalkylation
Pyridines - chemical synthesis
Pyridines - chemistry
sulfonates
sulfones
Sulfones - chemical synthesis
Sulfones - chemistry
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Summary:An efficient method for the synthesis of alkyl α,α‐difluorosulfonates has been developed. The selection of the 2‐pyridyl group as the aryl substitute on the sulfone is critically important for the success of this transformation (see scheme). The synthetic application of fluorinated sulfones is extended and a unique solution is provided for a long‐standing challenge in nucleophilic difluoro(sulfonato)methylation reactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201007594