Rhodium- and Iridium-Catalyzed Oxidative Coupling of Benzoic Acids with Alkynes via Regioselective C−H Bond Cleavage
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- 6 June 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (14) , 5362-5367
Abstract
The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl2]2 and Cu(OAc)2·H2O as catalyst and oxidant, respectively, to produce the corresponding isocoumarin derivatives. The copper salt can be reduced to a catalytic quantity under air. Interestingly, by using [Cp*IrCl2]2 in place of [Cp*RhCl2]2, the substrates undergo 1:2 coupling accompanied by decarboxylation to afford naphthalene derivatives exclusively. In this case, Ag2CO3 acts as an effective oxidant.Keywords
This publication has 26 references indexed in Scilit:
- Rhodium‐Catalyzed Coupling Reaction of Aroyl Chlorides with AlkenesAdvanced Synthesis & Catalysis, 2004
- Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen‐Coupled TurnoverAngewandte Chemie International Edition, 2004
- Rhodium‐Catalyzed Mizoroki–Heck‐Type Arylation of Alkenes with Aroyl Chlorides under Phosphane‐ and Base‐Free ConditionsAngewandte Chemie International Edition, 2003
- Iridium-Catalyzed Reaction of 1-Naphthols, N-(1-Naphthyl)benzenesulfonamides, and Salicylaldehyde with Internal AlkynesBulletin of the Chemical Society of Japan, 2001
- Iridium-Catalyzed Regioselective Reaction of 1-Naphthols with Alkynes at the peri-PositionChemistry Letters, 1999
- Reaction of 2-Hydroxybenzaldehydes with Alkynes, Alkenes, or Allenes via Cleavage of the Aldehyde C–H Bond Using a Rhodium Catalyst SystemBulletin of the Chemical Society of Japan, 1999
- Oxidative Cross-Coupling of N-(2‘-Phenylphenyl)benzene- sulfonamides or Benzoic and Naphthoic Acids with Alkenes Using a Palladium−Copper Catalyst System under AirThe Journal of Organic Chemistry, 1998
- Rhodium-Catalyzed Reaction of Aroyl Chlorides with AlkynesThe Journal of Organic Chemistry, 1996
- Rhodium-Catalyzed Reaction of Benzoic Anhydride with Styrene under Molecular HydrogenOrganometallics, 1995
- Mechanism of formation of 1,2,3,4-tetramethylnaphthalene from 2-butyne and triphenyltris(tetrahydrofuran) chromium(III)Journal of the American Chemical Society, 1970