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Volumn 46, Issue 31, 2007, Pages 5921-5924

Nickel-catalyzed coupling of arynes, alkenes, and boronic acids: Dual role of the boronic acid

Author keywords

Arynes; Boronic acids; Enones; Multicomponent reactions; Nickel

Indexed keywords

CATALYST ACTIVITY; NICKEL; PROTONS;

EID: 34547785103     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701063     Document Type: Article
Times cited : (79)

References (56)
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    • For examples of the application of this concept in total synthesis, see: a) E. A. Colby, K. C. O'Brien, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 4297;
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    • for recent application of this aryne precursors 1 in total synthesis, see: d U. K. Tambar, D. C. Ebner, B. M. Stoltz, J. Am. Chem. Soc. 2006, 128, 11752;
    • for recent application of this aryne precursors 1 in total synthesis, see: d) U. K. Tambar, D. C. Ebner, B. M. Stoltz, J. Am. Chem. Soc. 2006, 128, 11752;
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    • For a recent report on the metal-catalyzed cyclotrimerization of alkenes and arynes, see: I. Quintana, A. J. Boersma, D. Peña, D. Perez, E. Guitián, Org. Lett. 2006, 8, 3347.
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    • For an earlier report of boronic acids in nickel-catalyzed multicomponent reactions, see
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    • Even though, mechanistically, deuterium-labeling is expected at only one of the a carbons atoms, we obtained, approximately, an equal mixture of [D]4u and [D]4u′. This could be due to the scrambling of the deuterium between the a carbon atoms of the ketone catalyzed by CsF. Organoboronic acids acting as a proton source is proposed in literature; see: C. H. Oh, H. H. Jung, K. S. Kim, N. Kim, Angew. Chem. 2003, 115, 829;
    • Even though, mechanistically, deuterium-labeling is expected at only one of the a carbons atoms, we obtained, approximately, an equal mixture of [D]4u and [D]4u′. This could be due to the scrambling of the deuterium between the a carbon atoms of the ketone catalyzed by CsF. Organoboronic acids acting as a proton source is proposed in literature; see: C. H. Oh, H. H. Jung, K. S. Kim, N. Kim, Angew. Chem. 2003, 115, 829;
  • 49
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    • 2O at the end of the reaction.
    • 2O at the end of the reaction.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.