Journal
ISCIENCE
Volume 19, Issue -, Pages 749-+Publisher
CELL PRESS
DOI: 10.1016/j.isci.2019.08.021
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Funding
- Rutgers University
- NSF (CAREER) [CHE-1650766]
- NSFC [21702182, 21873081]
- Chinese Thousand Youth Talents Plan
- Zhejiang University
- NSF-MRI grant [CHE-1229030]
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The biaryl motif is a building block in many drugs, agrochemicals, and materials, and as such it is highly desirable as a synthesis target. The state-of-the-art process for biaryl synthesis from ubiquitous carboxylic acids is decarboxylative cross-coupling involving loss of carbon dioxide (CO2). However, the scope of these methods is severely limited, mainly due to specific substitution required to promote decarboxylation. The present report implements a decarbonylative version with loss of carbon monoxide (CO) that enables to directly engage carboxylic acids in a Suzuki-Miyaura cross-coupling to produce biaryls as a general method with high cross-coupling selectivity using a well-defined Pd(0)/(II) catalytic cycle. This protocol shows a remarkably broad scope (>80 examples) and is performed in the absence of exogenous inorganic bases. In a broader context, the approach shows promise for routine applications in the synthesis of biaryls by carefully controlled decarbonylation of prevalent carboxylic acids.
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