Enantioselective Scandium-Catalyzed Benzylic C−H Addition of Tertiary Anilines to Alkenes

IF 13.6 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI:10.1021/acscatal.6c05658

Xiangli Feng, Jiao Zhang, Qianlin Sun, Gen Luo, Xin Xu

引用次数: 0

Abstract

Enantioselective C−H addition of aromatic amines to alkenes represents a highly efficient and direct approach for the synthesis of chiral alkylanilines. Herein, we report an enantioselective benzylic C(sp³)−H addition of tertiary anilines to alkenes, enabled by a bulky anilido-oxazoline ligand-supported scandium catalyst. This protocol delivers a broad range of chiral alkylated anilines in high yields (up to 96%) and enantioselectivities (up to 98:2 e.r.). Furthermore, the obtained tertiary anilines are able to undergo facile C−N bond cleavage to afford enantioenriched aryl boronic esters and aryl silanes, serving as versatile intermediates for the synthesis of further functionalized, high-value molecules. The origins of chemo- and enantioselectivity in this transformation have been investigated through density functional theory calculations.

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叔苯胺在钪催化下对映选择性C−H加成烯烃

芳香胺对映选择性C−H加成烯烃是一种高效、直接的合成手性烷基苯胺的方法。在这里，我们报道了叔苯胺的对映选择性C(sp3)−H加成到烯烃上，由一个大体积的苯胺-恶唑啉配体负载的钪催化剂实现。该方案提供了广泛的手性烷基化苯胺的高收率（高达96%）和对映选择性（高达98:2 e.r）。此外，得到的叔苯胺能够进行容易的C−N键裂解，生成富集对映体的芳基硼酯和芳基硅烷，作为合成进一步功能化的高价值分子的多功能中间体。通过密度泛函理论计算，研究了这种转化中的化学和对映体选择性的起源。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.