Highly Active Catalyst for Suzuki–Miyaura Coupling to Form Sterically Demanding Biaryls: Electronic Control of Pd through the Secondary Interaction Using a Buchwald-Type Ligand Bearing a Fluorinated Aryl Ring

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-16 DOI:10.1021/acs.orglett.5c01467

Toshinobu Korenaga*, Hikaru Obata, Satsuki Moriya and Yuto Sakaizawa,

引用次数: 0

Abstract

To accelerate reductive elimination in Suzuki–Miyaura coupling (SMC) through secondary interactions with a Buchwald-type ligand, a heptafluorotolyl group was introduced into the ligand’s structure, guided by DFT calculations. The resulting ligand, HFTPhos, was effective for SMC, enabling the formation of sterically demanding biaryls. The catalyst loading could be reduced to as low as 0.025 mol % for tetra-ortho-substituted biaryls and 0.001 mol % for tri-ortho-substituted biaryls.

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Suzuki-Miyaura偶联形成空间要求高的双芳基的高活性催化剂：利用含氟芳基环的buchwald型配体通过二次相互作用对Pd的电子控制。

为了通过与buchwald型配体的二次相互作用加速Suzuki-Miyaura偶联（SMC）中的还原消除，在DFT计算的指导下，在配体结构中引入了七氟酰基。所得到的配体HFTPhos对SMC有效，能够形成要求立体的双芳基。四邻位取代双芳基的催化剂负载可降至0.025 mol %，三邻位取代双芳基的催化剂负载可降至0.001 mol %。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.