Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage.J Org Chem. 2007 Jul 06; 72(14):5362-7.JO
Abstract
The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl2]2 and Cu(OAc)2 x 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.
Pub Type(s)
Journal Article
Language
eng
PubMed ID
17550295
Citation
Ueura, Kenji, et al. "Rhodium- and Iridium-catalyzed Oxidative Coupling of Benzoic Acids With Alkynes Via Regioselective C-H Bond Cleavage." The Journal of Organic Chemistry, vol. 72, no. 14, 2007, pp. 5362-7.
Ueura K, Satoh T, Miura M. Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage. J Org Chem. 2007;72(14):5362-7.
Ueura, K., Satoh, T., & Miura, M. (2007). Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage. The Journal of Organic Chemistry, 72(14), 5362-7.
Ueura K, Satoh T, Miura M. Rhodium- and Iridium-catalyzed Oxidative Coupling of Benzoic Acids With Alkynes Via Regioselective C-H Bond Cleavage. J Org Chem. 2007 Jul 6;72(14):5362-7. PubMed PMID: 17550295.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage.
AU - Ueura,Kenji,
AU - Satoh,Tetsuya,
AU - Miura,Masahiro,
Y1 - 2007/06/06/
PY - 2007/6/7/pubmed
PY - 2007/6/7/medline
PY - 2007/6/7/entrez
SP - 5362
EP - 7
JF - The Journal of organic chemistry
JO - J Org Chem
VL - 72
IS - 14
N2 - The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl2]2 and Cu(OAc)2 x 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.
SN - 0022-3263
UR - https://www.unboundmedicine.com/medline/citation/17550295/Rhodium__and_iridium_catalyzed_oxidative_coupling_of_benzoic_acids_with_alkynes_via_regioselective_C_H_bond_cleavage_
L2 - https://doi.org/10.1021/jo070735n
DB - PRIME
DP - Unbound Medicine
ER -
