Journal
ACS CATALYSIS
Volume 11, Issue 10, Pages 5968-5973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01206
Keywords
iridium catalysis; terpyridine ligand; fluoroarene; borylation; rollover cyclometalation
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [JP20H04830]
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A terpyridine derivative and an iridium complex have been found to catalyze the C-H borylation of fluoroarenes with high ortho-selectivity and tolerance of various functional groups. This discovery could have important implications for the synthesis of complex drug molecules.
A terpyridine derivative and an iridium complex catalyze the C-H borylation of a stoichiometric amount of a fluoroarene with high ortho-selectivity and tolerance of functional groups such as bromide, chloride, ester, ketone, amine, and in situ-borylated hydroxyl. Complex drug molecules such as haloperidol can be selectively borylated ortho to the F atom. The terpyridine ligand undergoes rollover cyclometalation to produce an N,N,C-coordinated iridium complex, which may either selectively borylate the fluoroarene by itself or undergo reductive elimination to produce a borylated ligand.
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