Journal
ORGANOMETALLICS
Volume 30, Issue 17, Pages 4572-4577Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om200343b
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Funding
- National Science Foundation through the Center for Enabling New Technologies through Catalysis [CHE-0650456]
- North Carolina Biotechnology Center
- NCSU Department of Chemistry
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Catalytic H/D exchange reactions of benzene and benzoic acid with deuterated solvents have been studied using (Cp*IrCl2)(2). A 1:1 mixture of D2O/CD3OD produced the highest turnover numbers for benzene. High levels of deuterium incorporation into benzoic acid were observed only when sodium acetate was added to the reaction mixture. Attempts at producing hydroxybenzoic acid by catalytic C-H functionalization of benzoic acid with benzoquinone were unsuccessful. Instead, 2-hydroxy-6H-benzo[c]chromen-6-one was isolated as the major product. An array of substituted benzoic acids was analyzed for this functionalization reaction. Preliminary mechanistic studies indicate that the benzochromenones are formed by C-H bond activation of benzoic acid followed by insertion of benzoquinone into the iridium-carbon bond.
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