Borane/Gold(I)‐Catalyzed C−H Functionalization Reactions and Cycloaddition Reactions of Amines and α‐Alkynylenones

We present a strategy for the union of N-allylamines and carbonyl compounds by the concerted action of B(C 6 F 5 ) 3 and a N-based Brønsted base under redox-neutral conditions. The reaction of in situ generated conjugated iminium ions and enolates affords δ-aminocarbonyl com-pounds without waste generation. Furthermore, we describe that the cooperative action of B(C 6 F 5 ) 3 , a chiral Zn-based complex, and an amine facilitates the stereoselective reaction of a glycinate Schiff base ester and an N-allylamine to afford an α-substituted α-amino ester.

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α‐Alkylation of Mono‐Carbonyl Compounds with N‐Allylamines through Cooperative Actions of Lewis Acids and a Brønsted Base

Dai

Chapman

Wasa

2023

Asian J Org Chem

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Steric, Electronic and Conformational Synergistic Effects in the Gold(I)‐catalyzed α‐C−H Bond Functionalization of Tertiary Amines**

Rayo

Mansour

et al. 2022

Angewandte Chemie

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Direct CÀ H bond functionalization is a useful strategy for the straightforward formation of CÀ C and CÀ Heteroatom bonds. In the present work, a unique approach for the challenging electrophilic Au-catalyzed α-CÀ H bond functionalization of tertiary amines is presented. Electronic, steric and conformational synergistic effects exerted by the use of a malonate unit in the substrate were key to the success of this transformation. This new reactivity was applied to the synthesis of tetrahydro-γ-carboline products which, under oxidative conditions, could be converted into valuable structural motifs found in bioactive alkaloid natural products.

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Steric, Electronic and Conformational Synergistic Effects in the Gold(I)‐catalyzed α‐C−H Bond Functionalization of Tertiary Amines**

Rayo

Mansour

et al. 2022

Angew Chem Int Ed

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Borane/Gold(I)‐Catalyzed C−H Functionalization Reactions and Cycloaddition Reactions of Amines and α‐Alkynylenones

Abstract: We designed a borane/gold(I) co-catalytic system and used it for CÀ H functionalization reactions and cycloaddition reactions between tertiary amines and α-alkynylenones. Both reactions effectively incorporated a furan ring into the amine.

Cited by 3 publications

References 72 publications

α‐Alkylation of Mono‐Carbonyl Compounds with N‐Allylamines through Cooperative Actions of Lewis Acids and a Brønsted Base

α‐Alkylation of Mono‐Carbonyl Compounds with N‐Allylamines through Cooperative Actions of Lewis Acids and a Brønsted Base

Steric, Electronic and Conformational Synergistic Effects in the Gold(I)‐catalyzed α‐C−H Bond Functionalization of Tertiary Amines**

Steric, Electronic and Conformational Synergistic Effects in the Gold(I)‐catalyzed α‐C−H Bond Functionalization of Tertiary Amines**

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