Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 14, Pages 6163-6172Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c01630
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Funding
- National Institute of General Medical Sciences (NIGMS)
- NIH [R35GM134897-03]
- Princeton Catalysis Initiative
- Pfizer
- Merck
- Janssen
- Bristol Myers Squibb
- Genentech
- Princeton University
- Taylor family
- NSF [DGE-1656466]
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We have developed a photoinduced strategy that converts (hetero)aryl acids into aryl radicals for ambient-temperature borylation. This method operates under mild conditions and does not require prefunctionalization. Additionally, we have combined catalytic borylation with palladium-catalyzed Suzuki-Miyaura reactions to access a range of valuable products.
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.
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