Pd(II)-Catalyzed 1,2-Oxyarylation of Alkenes with O-Acylhydroxylamines as the Oxygen Source

Dao-Ming Wang; Lei Yang; Dong-Ping Chen; Yichen Wu; Yong Tang; Peng Wang

doi:10.1021/acs.orglett.4c00285

Pd(II)-Catalyzed 1,2-Oxyarylation of Alkenes with O-Acylhydroxylamines as the Oxygen Source

Org Lett. 2024 Apr 25. doi: 10.1021/acs.orglett.4c00285. Online ahead of print.

Authors

Dao-Ming Wang^{1

2}, Lei Yang², Dong-Ping Chen², Yichen Wu², Yong Tang^{1

2}, Peng Wang^{2

3

4}

Affiliations

¹ Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200062, P. R. China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road, Shanghai 200032, P. R. China.
³ School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou 310024, P. R. China.
⁴ College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry, and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. China.

PMID: 38662519
DOI: 10.1021/acs.orglett.4c00285

Abstract

O-Acylhydroxylamine has been widely employed as an electrophilic amination reagent in transition-metal-catalyzed C-N coupling reactions, but its use as an electrophilic oxygen source has not been disclosed. Here, we report a Pd-catalyzed 1,2-oxyarylation of alkenes with O-acylhydroxylamines as an oxidant and an oxygen source for the first time. With simple amide as the monodentate directing group, this method features a broad substrate scope, good functional group tolerance, and mild conditions.