Fluorination of arylboronic esters enabled by bismuth redox catalysis

被引：146

作者：

Planas, Oriol ^{[1
]}

Wang, Feng ^{[1
]}

Leutzsch, Markus ^{[1
]}

Cornella, Josep ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany

来源：

SCIENCE | 2020年 / 367卷 / 6475期

基金：

欧盟地平线“2020”;

关键词：

COPPER-MEDIATED FLUORINATION; MAIN-GROUP ELEMENTS; REDUCTIVE ELIMINATION; TRANSITION-METALS; ROOM-TEMPERATURE; BOND FORMATION; ARYL; DIFFUSION; PD; PHENYLATION;

D O I：

10.1126/science.aaz2258

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Bismuth catalysis has traditionally relied on the Lewis acidic properties of the element in a fixed oxidation state. In this paper, we report a series of bismuth complexes that can undergo oxidative addition, reductive elimination, and transmetallation in a manner akin to transition metals. Rational ligand optimization featuring a sulfoximine moiety produced an active catalyst for the fluorination of aryl boronic esters through a bismuth (III)/bismuth (V) redox cycle. Crystallographic characterization of the different bismuth species involved, together with a mechanistic investigation of the carbon-fluorine bond-forming event, identified the crucial features that were combined to implement the full catalytic cycle.

引用

页码：313 / +

页数：233

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