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Synthesis of Dihydroisobenzofuran Carboxaldehyde Derivatives by a Silver‐Catalyzed Sequential Protodesilylation/Cyclization/Oxidation Reaction
Author(s) -
Hamal Khagendra B.,
Sitaula Paban,
Chalifoux Wesley A.
Publication year - 2019
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.201801606
Subject(s) - chemistry , catalysis , scope (computer science) , dig , combinatorial chemistry , catalytic cycle , silylation , reaction conditions , organic chemistry , computer security , computer science , programming language
A new synthetic methodology has been developed for the synthesis of dihydroisobenzofuran carboxaldehyde derivatives. The reaction proceeds by a silver‐catalyzed protodesilylation/5‐exo‐dig cyclization/oxidation reaction to provide a broad scope of products with yields ranging from 55–91 %. Control experiments show that protodesilylation precedes the 5‐exo‐dig cyclization step in the catalytic cycle. The synthetic utility of these highly functionalized products was showcased through a number of chemoselective chemical transformations.