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Volumn 13, Issue 29, 2007, Pages 8333-8337

Rhodium-catalyzed [2+2+1+1] cyclocarbonylative coupling of alkynes with carbon monoxide affording tetrasubstituted p-benzoquinones

Author keywords

Alkynes; Benzoquinone; Carbonylation; Cycloaddition; Rhodium

Indexed keywords

CARBON MONOXIDE; CARBONYLATION; CATALYST ACTIVITY; CYCLOADDITION; FUNCTIONAL GROUPS; REACTION KINETICS; SUBSTITUTION REACTIONS;

EID: 35349007453     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700839     Document Type: Article
Times cited : (20)

References (54)
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    • For examples of the reports on the synthesis of p-benzoquinones see: a W. Adam, W. A. Herrmann. J. Lin, Ch. R. Saha-Moller. J. Org. Chem. 1994, 59, 8281-8283;
    • For examples of the reports on the synthesis of p-benzoquinones see: a) W. Adam, W. A. Herrmann. J. Lin, Ch. R. Saha-Moller. J. Org. Chem. 1994, 59, 8281-8283;
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    • The formation of p-benzoquinones from the reaction of the stoichiometric transition-metal carbonyl with alkynes has been reported. For examples of the reports see: a L. S. Liebeskind, J. P. Leeds, S. L. Baysdon, S. Iyer, J. Am. Chem. Soc 1984, 106, 6451-6453;
    • The formation of p-benzoquinones from the reaction of the stoichiometric transition-metal carbonyl with alkynes has been reported. For examples of the reports see: a) L. S. Liebeskind, J. P. Leeds, S. L. Baysdon, S. Iyer, J. Am. Chem. Soc 1984, 106, 6451-6453;
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    • The formation of p-benzoquinones as byproducts has been reported in the rhodium-catalyzed Pauson-Khand-type reactions see: T. Kobayashi, Y. Koga, K. Narasaka, J. Organomet. Chem. 2001, 624, 73-87;
    • The formation of p-benzoquinones as byproducts has been reported in the rhodium-catalyzed Pauson-Khand-type reactions see: T. Kobayashi, Y. Koga, K. Narasaka, J. Organomet. Chem. 2001, 624, 73-87;
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    • for ruthenium-catalyzed cross-carbonylation of alkynes and 2-norbornenes see reference [4a] ; for the rhodium-catalyzed [3+2] cycloaddition reaction of cyclopropenones and alkynes see : P. A. Wender, T. J. Paxton, T. J. Williams. J. Am. Chem. Soc. 2006, 128, 14814-14815.
    • for ruthenium-catalyzed cross-carbonylation of alkynes and 2-norbornenes see reference [4a] ; for the rhodium-catalyzed [3+2] cycloaddition reaction of cyclopropenones and alkynes see : P. A. Wender, T. J. Paxton, T. J. Williams. J. Am. Chem. Soc. 2006, 128, 14814-14815.
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    • 3], [RhCl(CO)(dppb)] (dppb = 1,4-bis(diphenylphosphino)butane), and [RhCl-(COd)(PPhMe2)] (cod = 1,5-cyclooctadiene) did not give 2a at all.
    • 3], [RhCl(CO)(dppb)] (dppb = 1,4-bis(diphenylphosphino)butane), and [RhCl-(COd)(PPhMe2)] (cod = 1,5-cyclooctadiene) did not give 2a at all.
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    • 13C NMR spectroscopy, see the Supporting Information.
    • 13C NMR spectroscopy, see the Supporting Information.
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    • CuI catalysis of the same transformation was reported see
    • CuI catalysis of the same transformation was reported see: A. V. Kel'in, V. Gevorgyan, J. Org. Chem. 2002, 67, 95-98.
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    • For examples of recent reports on the formation of maleoylmetal complexes from the reaction of alkyne with CO see: a M.-H. Cheng, H.-G. Syu, G.-H. Lee, S.-M. Peng, R.-S. Liu, Organometallics 1993, 12, 108-115;
    • For examples of recent reports on the formation of maleoylmetal complexes from the reaction of alkyne with CO see: a) M.-H. Cheng, H.-G. Syu, G.-H. Lee, S.-M. Peng, R.-S. Liu, Organometallics 1993, 12, 108-115;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.