Decarboxylative Borylation and Cross-Coupling of (Hetero)aryl Acids Enabled by Copper Charge Transfer Catalysis

被引:92
作者
Dow, Nathan W. [1 ]
Pedersen, P. Scott [1 ]
Chen, Tiffany Q. [1 ]
Blakemore, David C. [2 ]
Dechert-Schmitt, Anne-Marie [2 ]
Knauber, Thomas [2 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
[2] Pfizer Inc, Worldwide Res & Dev, Groton, CT 06340 USA
关键词
KINETIC CHARACTERISTICS; ORGANOBORON CHEMISTRY; PHOTOREDOX CATALYSIS; CONJUGATE ADDITION; AROYLOXYL RADICALS; BOND FORMATION; COMPLEXES; REAGENTS; CHLORIDE; BIARYLS;
D O I
10.1021/jacs.2c01630
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a copper-catalyzed strategy for arylboronic ester synthesis that exploits photoinduced ligand-to-metalcharge transfer (LMCT) to convert (hetero)aryl acids into aryl radicals amenable to ambient-temperature borylation. This near-UVprocess occurs under mild conditions, requires no prefunctionalization of the native acid, and operates broadly across diverse aryl,heteroaryl, and pharmaceutical substrates. We also report a one-pot procedure for decarboxylative cross-coupling that mergescatalytic LMCT borylation and palladium-catalyzed Suzuki-Miyaura arylation, vinylation, or alkylation with organobromides toaccess a range of value-added products. The utility of these protocols is highlighted through the development of a heteroselectivedouble-decarboxylative C(sp2)-C(sp2) coupling sequence, pairing copper-catalyzed LMCT borylation and halogenation processesof two distinct acids (including pharmaceutical substrates) with subsequent Suzuki-Miyaura cross-coupling.
引用
收藏
页码:6163 / 6172
页数:10
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