Remote meta-C–H α-Fluoro-alkenylation of Arenes Using gem-Difluoroalkenes

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-04-22 DOI:10.1021/acscatal.5c01455

Yogesh Bairagi, Sandip Porey, Iti Mahato, Debabrata Maiti

引用次数: 0

Abstract

Development of efficient and mild methods for the synthesis of arylated α-fluoroalkene motifs has attracted significant interest due to their broad applications in pharmaceuticals and agrochemicals. However, the synthesis of arylated α-fluoroalkenes has been limited to nondirected or directing group (DG)-assisted ortho-C(sp²)–H activation. Herein, we report the remote meta-selective α-fluoroalkenylation of arenes. Mechanistic studies have revealed the pivotal functions of a pyrimidine-based DG, palladium catalyst, hexafluoro-isopropanol (HFIP) solvent, and a monoprotected amino acid (MPAA) bidentate ligand in facilitating selective meta-C–H activation, leading to α-fluoroalkenylation with high regioselectivity.

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用宝石-二氟烯烃进行芳烃的远端间羟基α-氟烯化反应

由于芳基化α-氟烯烃基序在制药和农用化学品中的广泛应用，开发高效、温和的合成方法引起了人们的极大兴趣。然而，芳基化α-氟烯烃的合成仅限于非定向或定向基团（DG）辅助的正位c (sp2) -H活化。本文报道了芳烃的远端间选择性α-氟烯基化反应。机制研究揭示了基于嘧啶的DG、钯催化剂、六氟异丙醇（HFIP）溶剂和单保护氨基酸（MPAA）双齿配体在促进选择性间位c - h活化，导致具有高区域选择性的α-氟烯基化中的关键作用。

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.