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Lewis and Brønsted Acid Cocatalyzed Reductive Deoxyallenylation of Propargylic Alcohols with 2‐Nitrobenzenesulfonylhydrazide
Author(s) -
Liu Zhaohong,
Liao Peiqiu,
Bi Xihe
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404692
Subject(s) - brønsted–lowry acid–base theory , catalysis , lewis acids and bases , chemistry , steric effects , tertiary alcohols , substrate (aquarium) , reaction conditions , functional group , organic chemistry , reductive elimination , scope (computer science) , combinatorial chemistry , computer science , oceanography , polymer , geology , programming language
Reductive deoxyallenylation of sterically hindered tertiary propargylic alcohols was realized on reaction with 2‐nitrobenzenesulfonylhydrazide (NBSH) by the combined use of Lewis and Brønsted acid catalysts. This method features a broad substrate scope, mild reaction conditions, and good functional‐group tolerance, and affords various mono‐, di‐, and trisubstituted allenes in good‐to‐excellent yields. The synthetic utility of this method was demonstrated by the synthesis of 2 H ‐chromenes and 1,2‐dihydroquinolines.