Gold-Catalyzed Cyclization of Ynones Involving cis-Hydrofunctionalizations: Rapid Assembly of C-, O-, or S-Functionalized Pyrroles by a Single Methodology

Miaomiao Pei; Ali Wang; Xin Xie; Xiaoping Hu; Yuanhong Liu

doi:10.1021/acs.orglett.2c00205

Gold-Catalyzed Cyclization of Ynones Involving cis-Hydrofunctionalizations: Rapid Assembly of C-, O-, or S-Functionalized Pyrroles by a Single Methodology

Org Lett. 2022 Feb 25;24(7):1541-1545. doi: 10.1021/acs.orglett.2c00205. Epub 2022 Feb 10.

Authors

Miaomiao Pei^{1

2}, Ali Wang², Xin Xie², Xiaoping Hu², Yuanhong Liu^{1

2}

Affiliations

¹ Department of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou, Henan Province 450001, People's Republic of China.
² State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China.

PMID: 35142526
DOI: 10.1021/acs.orglett.2c00205

Abstract

A gold-catalyzed cyclization of conjugated ynones with various nucleophiles such as indoles, alcohols, and thiols has been developed. The reaction provides a new and efficient protocol for the synthesis of functionalized pyrroles with wide versatility and functional group compatibility. Remarkably, for indolyl, alkoxy, or sulfenyl pyrroles, all could be constructed efficiently by this single methodology. In addition, cis-hydrofunctionalizations of ynones are involved in these reactions.