Gold‐Catalyzed C(sp 3 )H/C(sp)H Coupling/Cyclization/Oxidative Alkynylation Sequence: A Powerful Strategy for the Synthesis of 3‐Alkynyl Polysubstituted Furans | Zendy

Ma Yuanhong | Zendy; Zhang Shuai | Zendy; Yang Shiping | Zendy; Song Feijie | Zendy; You Jingsong | Zendy

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Gold‐Catalyzed C(sp 3 )H/C(sp)H Coupling/Cyclization/Oxidative Alkynylation Sequence: A Powerful Strategy for the Synthesis of 3‐Alkynyl Polysubstituted Furans

Author(s) -

Ma Yuanhong,

Zhang Shuai,

Yang Shiping,

Song Feijie,

You Jingsong

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201402475

Subject(s) - chemistry , nucleophile , catalysis , alkynylation , aryl , combinatorial chemistry , domino , medicinal chemistry , coupling reaction , oxidative coupling of methane , alkyne , electrophile , organic chemistry , alkyl

In sharp contrast to the gold‐catalyzed reactions of alkynes/allenes with nucleophiles, gold‐catalyzed oxidative cross‐couplings and especially CH/CH cross‐coupling have been under represented. By taking advantage of the unique redox property and carbophilic π acidity of gold, this work realizes the first gold‐catalyzed direct C(sp 3 )H alkynylation of 1,3‐dicarbonyl compounds with terminal alkynes under mild reaction conditions, with subsequent cyclization and in situ oxidative alkynylation. A variety of terminal alkynes including aryl, heteroaryl, alkenyl, alkynyl, alkyl, and cyclopropyl alkynes all successfully participate in the domino reaction. The protocol offers a simple and region‐defined approach to 3‐alkynyl polysubstituted furans.

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