Enantioselective Synthesis of Ferrocene 1,3-Derivatives via Palladium/Norbornene Cooperative Catalysis

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-11-12 DOI:10.1021/acscatal.4c06231

Princi Gupta, Prakash Chandra Tiwari, Suchithra Madhavan, Manmohan Kapur

引用次数: 0

Abstract

Herein, we report a regio-and stereoselective distal C–H functionalization protocol for ferrocenes, leading to the synthesis of planar chiral ferrocene-1,3-derivatives by a Catellani-type reaction. The successful Pd(II)/norbornene catalyst combination can reach the inaccessible reaction site of ferrocene and accomplishes the selective C(3)-arylation of ferrocenyl methylamine. The ligand-controlled synergistic Pd/norbornene metal–organic cooperative catalysis under aerobic conditions successfully provides an array of ferrocene-1,3-derivatives in moderate-to-good yields with good enantio- and diastereoselectivities. A unique class of ferrocene 1,3-ligands, including PPFA-like and pincer type ligands bearing central and planar chirality, has been successfully synthesized by following this synthetic methodology.

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通过钯/降冰片烯协同催化对二茂铁 1,3-衍生物进行对映选择性合成

在此，我们报告了一种二茂铁的区域和立体选择性远端 C-H 功能化协议，通过卡泰拉尼型反应合成平面手性二茂铁-1,3-衍生物。成功的钯(II)/降冰片烯催化剂组合可以到达二茂铁难以进入的反应位点，并完成二茂铁甲胺的选择性 C(3)-芳基化反应。在有氧条件下，配体控制的钯/降冰片烯金属有机协同催化成功地提供了一系列二茂铁-1,3-衍生物，产率从中等到良好，并具有良好的对映和非对映选择性。通过这种合成方法，成功合成了一类独特的二茂铁 1,3 配体，包括具有中心和平面手性的 PPFA 样配体和钳型配体。

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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.