Rhodium-/Iridium-Catalyzed Hydroamination for the Synthesis of 1,2-, 1,3-, or 1,4-Diamines

被引：8

作者：

Ho, An T. ^{[1
]}

Ensign, Seth C. ^{[2
]}

Vanable, Evan P. ^{[2
]}

Portillo, David ^{[1
]}

Humke, Jenna N. ^{[2
]}

Kortman, Gregory D. ^{[2
]}

Hull, Kami L. ^{[1
,2
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78741 USA

[2] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ACS CATALYSIS | 2022年 / 12卷 / 14期

关键词：

hydroamination; iridium catalysis; rhodium catalysis; diamine; regiodivergent; ANTI-MARKOVNIKOV ADDITION; INTERMOLECULAR HYDROAMINATION; UNACTIVATED ALKENES; BITE ANGLE; INTRAMOLECULAR HYDROAMINATION; SECONDARY ALKYL; OXIDATIVE ADDITION; TERMINAL ALKYNES; PRIMARY AMINES; FUNCTIONALIZATIONS;

D O I：

10.1021/acscatal.2c01835

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The Ir-catalyzed regioselective hydroamination of allyl amines as well as the catalyst-controlled regiodivergent hydroamination of homoallylic amines with aniline nucleophiles is reported. These directed hydroamination reactions afford a variety of 1,2-, 1,3-, and 1,4-diamines in good to excellent yields and high regio- and chemoselectivities. Mechanistic investigations suggest that the reactions are proceeding through an oxidative addition into the ArHN-H bond and that the observed regioselectivity is due to the selective formation of a five- or six-membered metallacyclic intermediate depending on the catalyst employed.

引用

页码：8331 / 8340

页数：10

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