A general system achieving three-component
intermolecular carbofunctionalization
of alkenes is presented, including carboetherification, carboesterification,
carboarylation, and carboamination. The scope of the reaction is presented
with respect to the carbon electrophile, the olefin, and the nucleophile.
Furthermore, the synthesis of γ-lactams via a carboamination reaction is demonstrated in a telescoped three-step
protocol.
Catalytic carbonylations of aryl electrophiles via C(sp 2 )À N cleavage remains a significant challenge. Herein, we demonstrate an aminocarbonylation of aniline-derived trialkylammonium salts promoted by visible light with a simple cobalt catalyst. The reaction proceeds under mild conditions suitable for late-stage functionalization and is amenable to telescoped carbonylations directly from anilines. A range of alkylamines are successful partners, and alkoxycarbonylation is also demonstrated. Mechanistic studies and DFT calculations support a novel mechanism for catalytic carbonylations of aryl electrophiles involving a key visible light-induced carbonyl photodissociation.
A general system achieving three-component intermolecular carbofunctionalization of alkenes is presented. A range of substituted alkenes are functionalized with α-bromo carbonyl electrophiles and nitrogen, oxygen, and carbon nucleophiles. Mechanistic findings support the intermediacy of a cyclic oxocarbenium ion.
A general system achieving three-component intermolecular carbofunctionalization of alkenes is presented. A range of substituted alkenes are functionalized with α-bromo carbonyl electrophiles and nitrogen, oxygen, and carbon nucleophiles. Mechanistic findings support the intermediacy of a cyclic oxocarbenium ion.
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