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Bifunctional Ligand Enables Efficient Gold‐Catalyzed Hydroalkenylation of Propargylic Alcohol
Author(s) -
Liao Shengrong,
Porta Alessio,
Cheng Xinpeng,
Ma Xu,
Zai Giuseppe,
Zhang Liming
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201802533
Subject(s) - ligand (biochemistry) , catalysis , bifunctional , alkene , intermolecular force , chemistry , alcohol , combinatorial chemistry , biphenyl , conjugated system , stereochemistry , organic chemistry , molecule , biochemistry , polymer , receptor
Using the previously designed biphenyl‐2‐ylphosphine ligand, featuring a remote tertiary amino group, the first gold‐catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general‐base catalyst for promoting this novel gold catalysis with good efficiency.