Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters

被引：19

作者：

Blackburn, J. Miles ^{[1
]}

Kanegusuku, Anastasia L. Gant ^{[1
]}

Scott, Georgia E. ^{[1
]}

Roizen, Jennifer L. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Box 90346, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

基金：

美国国家卫生研究院;

关键词：

SUZUKI-MIYAURA REACTIONS; CROSS-COUPLING REACTIONS; N BOND FORMATION; ARYL; AMINATION; PHOTOREDOX; ACID; ARYLATION; HALIDES; LIGAND;

D O I：

10.1021/acs.orglett.9b02621

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O-alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N-alkylation, which was found to plague palladium-based protocols for N-arylation of O-alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C-N coupling processes.

引用

页码：7049 / 7054

页数：6

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