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2,2′‐Bis‐substituted Biphenyls by the Addition of Nucleophiles to Benzyne Followed by In Situ Oxidative Homocoupling
Author(s) -
Sibbel Friederike,
Daniliuc Constantin G.,
Studer Armido
Publication year - 2015
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.201500456
Subject(s) - aryne , chemistry , nucleophile , in situ , oxidative phosphorylation , adduct , medicinal chemistry , nucleophilic addition , catalysis , organic chemistry , biochemistry
The paper describes the addition of Mg‐anilides and ‐thiolates to in situ generated benzyne with subsequent oxidative homocoupling of the adducts to give 2,2′‐bis‐substituted biphenyls in a one‐pot process. Oxidative C–C bond formation was best achieved with a Cu catalyst using O 2 as oxidant. The sequence comprises two C–X and one C–C bond formation and the products were obtained in moderate yields. Some of the 2,2′‐bis‐substituted biphenyls have been characterized by X‐ray analysis.