Synthesis 2022; 54(01): 161-170
DOI: 10.1055/a-1581-2408
paper

p-Toluenesulfonic Acid-Catalyzed Reaction of Phthalaldehydic Acids with Difluoroenoxysilanes: Access to 3-Difluoroalkyl Phthalides

Saimei Liu
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
,
Yan Li
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
,
Feiyi Wang
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
,
Chao Ma
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
,
Guichun Yang
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
,
Jianguo Yang
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
b   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. China
,
Jun Ren
a   Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Hubei University, Wuhan 430062, P.R. China
› Author Affiliations

This work was supported by the National Natural Science Foundation of China (NSFC. 21676075).


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Abstract

A convenient approach for the synthesis of 3-difluoroalkyl phthalides has been developed from phthalaldehydic acids and difluoroenoxysilanes by using relatively inexpensive p-toluenesulfonic acid monohydrate (PTSA) as a catalyst. A series of 3-difluoroalkyl phthalides and cyclic difluoroalkyl ethers were obtained in up to 99% yield. The products obtained could be readily converted into difluoroalkyl phthalide derivatives by simple modifications.

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Publication History

Received: 17 June 2021

Accepted after revision: 09 August 2021

Accepted Manuscript online:
09 August 2021

Article published online:
09 September 2021

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