The Suzuki-Miyaura reaction

作者: Ivica Cepanec

DOI: 10.1016/B978-008044412-3/50006-3

关键词: Organoboron compoundsHalideGrignard reactionChemistryArylElectrophileOrganic chemistry

摘要: The cross-coupling reactions of a wide variety organoboron compounds with aryl halides and similar substrates, such as sulfonates or some other electrophilic to produce alkenes, arylalkenes, alkylarenes, biaryls are well known the Suzuki–Miyaura (SM) reaction, which due its general applicability efficiency has become most important C–C bond-forming “Grignard reaction 21 st century.” applications in synthesis discussed this chapter. SM includes arylboronic acids esters (Ar – X, X = I, Br, C1), (ArOTf OMs), diazonium salts (ArN 2 + BF 4 ), proceeds smoothly give corresponding good excellent yields.

参考文章(170)
Miki Murata, Takashi Oyama, Shinji Watanabe, Yuzuru Masuda, Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates Journal of Organic Chemistry. ,vol. 65, pp. 164- 168 ,(2000) , 10.1021/JO991337Q
Xiaohong Bei, Thomas Crevier, Anil S. Guram, Bernd Jandeleit, Timothy S. Powers, Howard W. Turner, Tetsuo Uno, W.Henry Weinberg, A convenient palladium/ligand catalyst for Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides Tetrahedron Letters. ,vol. 40, pp. 3855- 3858 ,(1999) , 10.1016/S0040-4039(99)00642-5
Nicholas E. Leadbeater, Maria Marco, Rapid and amenable suzuki coupling reaction in water using microwave and conventional heating. Journal of Organic Chemistry. ,vol. 68, pp. 888- 892 ,(2003) , 10.1021/JO0264022
Qiao-Sheng Hu, Dilrukshi Vitharana, Xiao-Fan Zheng, Chi Wu, Chi Man Simon Kwan, Lin Pu, Poly(1,1‘-bi-2-naphthol)s: Synthesis, Characterization, and Application in Lewis Acid Catalysis Journal of Organic Chemistry. ,vol. 61, pp. 8370- 8377 ,(1996) , 10.1021/JO961407I
J-J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, A Highly Active Suzuki Catalyst for the Synthesis of Sterically Hindered Biaryls: Novel Ligand Coordination Journal of the American Chemical Society. ,vol. 124, pp. 1162- 1163 ,(2002) , 10.1021/JA017082R
Akira Suzuki, Organoboron compounds in new synthetic reactions Pure and Applied Chemistry. ,vol. 57, pp. 1749- 1758 ,(1985) , 10.1351/PAC198557121749
Jian-Yang Cho, Carl N. Iverson, Milton R. Smith, Steric and Chelate Directing Effects in Aromatic Borylation Journal of the American Chemical Society. ,vol. 122, pp. 12868- 12869 ,(2000) , 10.1021/JA0013069