Homogeneous and Nanoparticle Gold-Catalyzed Hydrothiocyanation of Haloalkynes

Xiaojun Zeng; Bocheng Chen; Zhichao Lu; Gerald B Hammond; Bo Xu

doi:10.1021/acs.orglett.9b00728

Homogeneous and Nanoparticle Gold-Catalyzed Hydrothiocyanation of Haloalkynes

Org Lett. 2019 Apr 19;21(8):2772-2776. doi: 10.1021/acs.orglett.9b00728. Epub 2019 Apr 9.

Authors

Xiaojun Zeng¹, Bocheng Chen², Zhichao Lu¹, Gerald B Hammond¹, Bo Xu²

Affiliations

¹ Department of Chemistry , University of Louisville , Louisville , Kentucky 40292 , United States.
² College of Chemistry, Chemical Engineering and Biotechnology , Donghua University , 2999 North Renmin Lu , Shanghai , China.

PMID: 30964693
DOI: 10.1021/acs.orglett.9b00728

Abstract

The first homogeneous and heterogeneous nanoparticle gold-catalyzed addition of sulfur nucleophiles to alkynes was developed. More specifically, gold-catalyzed hydrothiocyanation of haloalkynes gave good yields and good stereoselectivity of vinyl thiocyanates. Furthermore, a sulfur-based gold catalyst (PPh₃AuSCN) has shown a unique reactivity in gold-catalyzed reactions such as the cyclization of N-propargylic amides.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.