Journal
SCIENCE
Volume 375, Issue 6581, Pages 658-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.abm7599
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [20H04830]
- Grants-in-Aid for Scientific Research [20H04830] Funding Source: KAKEN
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Regioselective functionalization of arenes is a challenging problem in organic synthesis. This study presents a strategy based on remote steric control, where a roof-like ligand protects the distant para site and enables selective activation of meta carbon-hydrogen (C-H) bonds.
Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy based on remote steric control, whereby a roof-like ligand protects the distant para site in addition to the ortho sites, and thereby enables selective activation of meta carbon-hydrogen (C-H) bonds in the absence of ortho or para substituents. We demonstrate this concept for iridium-catalyzed meta-selective borylation of various monosubstituted arenes, including complex drug molecules. This strategy has the potential to expand the toolbox of C-H bond functionalization to previously nondifferentiable reaction sites.
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