Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and onl...

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Bibliographic Details
Published inChemical papers Vol. 74; no. 10; pp. 3303 - 3310
Main Authors Yu, Shu-Yan, Gao, Li-Hong, Wu, Jing-Xin, Lan, Hong-Bing, Ma, Yi, Yin, Zhi-Gang
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 01.10.2020
Springer Nature B.V
Subjects
Biochemistry
Biotechnology
Cesium
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Industrial Chemistry/Chemical Engineering
Materials Science
Medicinal Chemistry
Original Paper
Stereoselectivity
Transition metals
Cesium carbonate
Intramolecular hydroalkoxylation
Transition-metal-free
Dihydroisobenzofurans
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Summary:An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z -isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.
ISSN:2585-7290
0366-6352
1336-9075
DOI:10.1007/s11696-020-01159-5