Palladium-Catalyzed NHC Ligand-Controlled Regiodivergent Allyl-Fluoroallyl Cross-Couplings

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-21 DOI:10.1039/d4qo01800a

Yangyang Ma, Boxia Xu, Hua Zhang, Zhiping Li

引用次数: 0

Abstract

The palladium-catalyzed cross-coupling of (E)-2-fluoroallyl carbonates and allylboronates is reported. The regioselectivity is susceptive to the steric requirements of the NHC ligand, with small IMes favoring the linear fluorinated 1,5-dienes, while the IPrBIDEA featuring sterically-congested character benefits the branched products. Control experiments revealed that either 2-fluoroallyl carbonates or gem-F2CPs could undergo allylation with excellent regioselectivity, yet the former behaved with some lower branched reactivity.

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钯催化的 NHC 配体控制的 Regiodivergent 烯丙基-氟烯丙基交叉耦合反应

报告了钯催化 (E)-2- 氟烯丙基碳酸酯和烯丙基硼酸酯的交叉偶联。其区域选择性易受 NHC 配体立体要求的影响，小的 IMes 有利于线性氟化 1,5 二烯，而具有立体拥挤特征的 IPrBIDEA 则有利于支链产物。对照实验表明，2-氟烯丙基碳酸盐或 gem-F2CPs 都能以极好的区域选择性进行烯丙基化反应，但前者的支化反应活性较低。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.