Novel Sulfinamide-Based Chiral Ligand Promoted Chiral Diarylmethanol Preparation via exo-Directed Asymmetric C–H Alkynylation under Mild Conditions

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-01-28 DOI:10.1021/acscatal.4c07549

Xin Yu, Siqi Liu, Lei Wang, Ya Li, Meirong Huang, Zheng-Yang Yan, Hao-Chen Li, Qi Zhang, Xinhao Zhang, Bing-Feng Shi

引用次数: 0

Abstract

Desymmetrization of diarylmethanols has been achieved by means of exo-directed Pd(II)-catalyzed C–H alkynylation under mild conditions (30 °C). We herein designed a class of chiral N-sulfinyl anthranilic acid (CSAA) ligands with chiral information only at the N-protecting group, which were found crucial for challenging stereocontrol within a conformationally flexible exo-chelated six-membered palladacycle. An array of valuable chiral diarylmethanols were obtained in high yield, good enantioselectivity, and broad functional group tolerance. Gram-scale synthesis was readily carried out and a diverse range of transformations were implemented with high retention of configuration, highlighting the synthetic utility of this method. Preliminary mechanistic studies indicated that CSAAs adopted an N,O-chelation mode, and the chiral induction proceeded through direct interaction between the N-tert-butanesulfinamide motif with the substrate.

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新型亚磺酰胺基手性配体在温和条件下通过外向不对称 C-H 烷炔化作用促进手性二甲基甲醇的制备

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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.