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Catalyst‐Free Synthesis of α‐Functionalized 2 H ‐Chromenes in Water: A Tandem Self‐Promoted pseudo ‐Substitution and Decarboxylation Process
Author(s) -
Jiang Chunhui,
Chen Yayun,
Zhang Hongkui,
Tan JianPing,
Wang Tianli
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900641
Subject(s) - decarboxylation , tandem , catalysis , chemistry , substrate (aquarium) , reactivity (psychology) , combinatorial chemistry , organic chemistry , reaction conditions , cascade reaction , materials science , medicine , oceanography , alternative medicine , pathology , composite material , geology
A catalyst‐free decarboxylative reaction between β‐keto acids and 2 H ‐chromene acetals in water was developed. This reaction featured a broad substrate scope and easily obtainable starting materials to afford α‐functionalized 2 H ‐chromenes in high yields. The synthetic value of this protocol was also demonstrated by the scale‐up synthesis and versatile conversions of the title product into other useful compounds. In addition, control experiments indicated that water was essential for the reactivity. Mechanistic studies further revealed that the reaction proceeded through a self‐promoted tandem pseudo ‐substitution and decarboxylation process.