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Direct Cross‐Couplings of Propargylic Diols
Author(s) -
Green Nicholas J.,
Willis Anthony C.,
Sherburn Michael S.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604527
Subject(s) - aryl , chemistry , halogen , sequence (biology) , boronic acid , combinatorial chemistry , diol , stereochemistry , stereoisomerism , organic chemistry , molecule , biochemistry , alkyl
[Pd(PPh 3 ) 4 ] catalyzes a Suzuki–Miyaura‐like twofold cross‐coupling sequence between underivatized propargylic diols and either aryl or alkenyl boronic acids to furnish highly substituted 1,3‐dienes. Thus, 2,3‐diaryl‐1,3‐butadienes and their dialkenic congeners ([4]dendralenes) are delivered in a (pseudo)halogen‐free, single‐step synthesis which supersedes existing methods. Allenols are also readily formed. Treatment of these single‐ and twofold cross‐coupled products with acid leads to remarkably short syntheses of highly‐substituted benzofulvenes and aryl indenes, respectively.