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Volumn , Issue 22, 2009, Pages 3688-3692

A general and efficient suzuki-miyaura cross-coupling protocol using weak base and no water: The essential mole of acetate

Author keywords

Boranes; Cross coupling; Lewis bases; Palladium; Suzuki miyaura coupling

Indexed keywords


EID: 67650717993     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900538     Document Type: Article
Times cited : (19)

References (72)
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    • However, this paper does not seem to cover the mechanism of B-alkyl coupling. For a recent DFT study of the role of the base in Suzuki coupling, see
    • For a recent DFT study of the role of the base in Suzuki coupling, see: A. A. C. Braga, N. H. Morgon, G. Ujaque, F. Maseras, J. Am. Chem. Soc. 2005, 127, 9293-9307. However, this paper does not seem to cover the mechanism of B-alkyl coupling.
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    • This situation parallels that of Stille coupling, for a review, see: P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808-4839;
    • This situation parallels that of Stille coupling, for a review, see: P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808-4839;
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    • a3 12.67) is a much stronger base. For a survey of the acidity of boronic acids, see: D. G. Hall (Ed.: D. G. Hall) in Boronic Acids Wiley-VCH, Weinheim, 2005, pp. 10.
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    • Thus, through p-π conjugation, the car-bonyl oxygen atom in TS2 is apparently more basic and nucleo-philic than those of ordinary carbonyl species. Even the latter coordinated with organoboranes, see: b L. A. Duncanson, W. Gerrard, M. F. Lappert, H. Pyszora, R. Schafferman, J. Chem. Soc. 1958, 3652-3656;
    • Thus, through p-π conjugation, the car-bonyl oxygen atom in TS2 is apparently more basic and nucleo-philic than those of ordinary carbonyl species. Even the latter coordinated with organoboranes, see: b) L. A. Duncanson, W. Gerrard, M. F. Lappert, H. Pyszora, R. Schafferman, J. Chem. Soc. 1958, 3652-3656;
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    • Recently, Garg and Shi reported the Ni-catalyzed Suzuki-type cross-coupling of aryl carboxylates, for which an analogous six-membered transition state was also proposed to explain the transmetalation to nickel: a K. W. Quasdorf, X. Tian, N. Garg, J. Am. Chem. Soc. 2008, 130, 14422-14423;
    • Recently, Garg and Shi reported the Ni-catalyzed Suzuki-type cross-coupling of aryl carboxylates, for which an analogous six-membered transition state was also proposed to explain the transmetalation to nickel: a) K. W. Quasdorf, X. Tian, N. Garg, J. Am. Chem. Soc. 2008, 130, 14422-14423;


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