Journal
ORGANOMETALLICS
Volume 29, Issue 9, Pages 2001-2003Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om1000887
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Funding
- Research Grants Council of Hong Kong of the SAR of China [400308]
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Selective carbonyl carbon (C(=O)) and alpha-carbon (C(methyl)) bond activation of acetophenones was discovered by the high-valent, iridium(III)5,10,15,20-tetrakis-4-tolylporphyrinato carbonyl chloride (Ir(ttp)Cl(CO)), which also acted as a Lewis acid in catalyzing the aldol condensation of acetophenones together with release of the coproduct water. Preliminary mechanistic studies suggest that both aliphatic and aromatic carbon-hydrogen bond activation products are kinetic products, which can be converted by reaction with water to iridium porphyrin hydride (Ir(ttp)H) via iridium porithyrin hydroxide (Ir(ttp)OH). Both Ir(ttp)OH and Ir(ttp)H were the possible intermediates to cleave the C(=O)-C(methyl) bond of acetophenones and to generate iridium porphyrin acyl complexes as the thermodynamic products.
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