Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals

被引:175
作者
Nielsen, Matthew K. [1 ]
Shields, Benjamin J. [1 ]
Liu, Junyi [1 ]
Williams, Michael J. [2 ]
Zacuto, Michael J. [2 ]
Doyle, Abigail G. [1 ]
机构
[1] Princeton Univ, Dept Chem, 120 Washington Rd, Princeton, NJ 08544 USA
[2] Celgene Corp, Drug Substance Dev, 556 Morris Ave, Summit, NJ 07901 USA
关键词
C-H functionalization; formylation; nickel; photocatalysis; redox reactions; PALLADIUM-CATALYZED FORMYLATION; CARBON-MONOXIDE; HALIDES; ALDEHYDES; BROMIDES; CARBONYLATION;
D O I
10.1002/anie.201702079
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.
引用
收藏
页码:7191 / 7194
页数:4
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