乙烯基环丙烷：控制环加成反应中线性区域选择性的全碳偶极前驱体

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-06-20 DOI:10.1021/acscatal.5c01939

Na Lin, Jun-Tao Chen, Yang-Zi Liu, Wei-Ping Deng

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引用次数: 0

摘要

通过光催化合成了乙烯基环丙烷（VACP），并将其作为1,5-全碳偶极前驱体用于钯催化的[5 + n]环加成与线性（aza）二烯或亚甲基亚胺。该方法提供8 - 9元（aza）循环，收率高达95%，具有独特的线性区域选择性和对不同官能团的高耐受性。这种合成方法的可行性通过放大反应和随后的转化得到了证实。这些发现突出了VACP作为区域选择性环加成反应的通用试剂的重要效用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Vinylarylcyclopropanes (VACPs): All-Carbon Dipole Precursors for Controlling Linear Regioselectivity in Cycloaddition Reactions

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Vinylarylcyclopropanes (VACPs): All-Carbon Dipole Precursors for Controlling Linear Regioselectivity in Cycloaddition Reactions

A vinylarylcyclopropane (VACP) was synthesized via photocatalysis and employed as a 1,5-all-carbon dipole precursor in palladium-catalyzed [5 + n] cycloadditions with linear (aza)dienes or azomethine imines. This method affords eight- to nine-membered (aza)cycles in yields of up to 95%, displaying exclusive linear regioselectivity and high tolerance toward diverse functional groups. The viability of this synthetic approach was confirmed through scaled-up reactions and subsequent transformations. These findings highlight the significant utility of VACP as a versatile reagent for regioselective cycloaddition reactions.

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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.