Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp2)-C(sp3) Cross-Couplings in Flow

被引：157
作者：
Lima, Fabio [1 ]
Kabeshov, Mikhail A. [1 ]
Tran, Duc N. [1 ]
Battilocchio, Claudio [1 ]
Sedelmeier, Joerg [2 ]
Sedelmeier, Gottfried [2 ]
Schenkel, Berthold [2 ]
Ley, Steven V. [1 ]
机构：
[1] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England
[2] Novartis Pharma AG, Novartis Campus, CH-4002 Basel, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 45期
基金：
英国工程与自然科学研究理事会;
关键词：
boronic esters; cross-coupling; flow chemistry; photoredox catalysis; synthetic methods; SINGLE-ELECTRON TRANSMETALATION; C-H BONDS; DUAL CATALYSIS; ORGANIC-SYNTHESIS; NICKEL CATALYSIS; DIRECT ARYLATION; BENZYLIC ETHERS; DIAZO-COMPOUNDS; ARYL; ALKYL;
D O I：
10.1002/anie.201605548
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high-throughput continuous flow process was developed to perform a dual iridium- and nickel-catalyzed C(sp(2))-C(sp(3)) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine-derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp(2))-C(sp(3)) coupling method using boronic esters and cyano heteroarenes under flow conditions.
引用
收藏
页码：14085 / 14089
页数：5
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