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拓展原位生成的 α-氧代金卡宾的分子间捕获范围：通过 C-C 键形成实现烯丙基砜和末端炔烃的高效氧化偶联。

Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation.

机构信息

Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106.

College of Science, China Pharmaceutical University, Nanjing, 210009, P. R. China.

出版信息

Chem Commun (Camb). 2014 Apr 21;50(31):4130-4133. doi: 10.1039/c4cc00739e.

DOI:10.1039/c4cc00739e
PMID:24622909
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4090113/
Abstract

With a new P,S-bidentate phosphine as the ligand to gold(I), the α-oxo gold carbenes generated in situ via gold-catalyzed intermolecular oxidation of terminal alkynes were effectively trapped by various allylic sulfides, resulting in the formation of α-aryl(alkyl)thio-γ,δ-unsaturated ketones upon facile [2,3]sigmatropic rearrangements.

摘要

采用新型 P,S-双齿膦配体作为金（I）催化剂，通过金催化末端炔烃的分子间氧化原位生成的α-氧代金卡宾可被各种烯丙基硫醚有效地捕获，随后经易发生的[2,3]σ迁移重排反应生成α-芳基（烷基）硫代-γ,δ-不饱和酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6cee/4090113/608d2457a5fc/nihms-599297-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6cee/4090113/4d4e5923f271/nihms-599297-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6cee/4090113/608d2457a5fc/nihms-599297-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6cee/4090113/4d4e5923f271/nihms-599297-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6cee/4090113/608d2457a5fc/nihms-599297-f0002.jpg

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2
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J Am Chem Soc. 2013 Jun 5;135(22):8197-200. doi: 10.1021/ja4040895. Epub 2013 May 24.
3
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