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Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity.

ABSTRACT: In the presence of a neutral dppf-modified iridium catalyst and Cs2CO3, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate-directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine.

SUBMITTER: Kim SW 

PROVIDER: S-EPMC6264884 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity.

Kim Seung Wook SW   Wurm Thomas T   Brito Gilmar A GA   Jung Woo-Ok WO   Zbieg Jason R JR   Stivala Craig E CE   Krische Michael J MJ  

Journal of the American Chemical Society 20180710 29

In the presence of a neutral dppf-modified iridium catalyst and Cs<sub>2</sub>CO<sub>3</sub>, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate-directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine. ...[more]

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