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Metal‐Free Alkenylation of Salicylaldehydes with Boronic Acids: Synthesis of Skipped Dienes and 2 H ‐Chromenes
Author(s) -
Harris Dylan H.,
Barichello Renata O.,
Bolshan Yuri
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001019
Subject(s) - chemistry , organic chemistry , metal , salicylaldehyde , boronic acid , ether , polymer chemistry , schiff base
Metal‐free alkenylation of salicylaldehydes and the preparation of 2 H ‐chromenes have been developed. Reactions occur in the presence of tetrafluoroboric acid diethyl ether complex. Vinylboronic acid derivatives including indeneboronic acid react readily with salicylaldehydes to afford the corresponding skipped dienes. When 6‐bromo or 6‐chlorosalicylaldehydes are submitted to the reaction conditions the formation of 2 H ‐chromenes is observed in good to excellent yields.