Auxiliary‐Based Stereoconvergent Transition Metal‐Free Cross‐Electrophile Couplings of α‐Iodoboronic Esters

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-09-10 DOI:10.1002/adsc.70117

Max Schwenzer, Armido Studer

引用次数: 0

Abstract

Chiral boronic esters are highly valuable building blocks in organic chemistry and related fields, allowing access to structurally diverse libraries, including those of drug candidates. Herein, stereoselective cross couplings of α‐iodoboronic esters with various commercial electrophiles are reported. These stereoconvergent coupling reactions proceed via iodine‐metal exchange and subsequent stereoselective capture of the generated α‐boryl organometallic species without the use of a transition metal catalyst. The presented reactions allow the α‐silylation, α‐borylation, and α‐methylborylation of boronic esters using a common chiral auxiliary.

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辅助基立体会聚过渡金属自由交叉亲电偶联α -碘硼酯

手性硼酯是有机化学和相关领域非常有价值的构建模块，允许访问结构多样的文库，包括候选药物的文库。本文报道了α‐碘硼酯与各种商业亲电试剂的立体选择性交叉偶联。这些立体会聚偶联反应通过碘-金属交换和随后的立体选择性捕获生成的α -硼基有机金属，而无需使用过渡金属催化剂。所提出的反应允许使用共同的手性助剂对硼酯进行α‐硅基化、α‐硼基化和α‐甲基硼基化。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.