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One‐Pot Cannizzaro Cascade Synthesis of ortho ‐Fused Cycloocta‐2,5‐dien‐1‐ones from 2‐Bromo(hetero)aryl Aldehydes
Author(s) -
Burroughs Laurence,
Eccleshare Lee,
Ritchie John,
Kulkarni Omkar,
Lygo Barry,
Woodward Simon,
Lewis William
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505347
Subject(s) - chemistry , allene , aryl , intramolecular force , propargyl , hydride , combinatorial chemistry , ring (chemistry) , propargyl alcohol , medicinal chemistry , organic chemistry , catalysis , alkyl , hydrogen
An intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene enables the synthesis of ortho‐fused 4‐substituted cycloocta‐2,5‐dien‐1‐ones with unprecedented technical ease for an eight‐ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.