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Volumn 46, Issue 28, 2007, Pages 5359-5363

Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies

Author keywords

Boronate esters; Borylation; C C coupling; Palladium; Suzuki Miyaura coupling

Indexed keywords

BIARYL PRODUCTS; BORONATE ESTERS; BORYLATION; CATALYTIC CYCLE; SUZUKI-MIYAURA COUPLING;

EID: 34447569410     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701551     Document Type: Article
Times cited : (315)

References (28)
  • 3
    • 84889487088 scopus 로고    scopus 로고
    • Structure, Properties, and Preparation of Boronic Acid Derivatives: D. G. Hall in Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine (Ed.: D. G. Hall) Wiley-VCH, Weinheim, 2005, pp. 1-99.
    • "Structure, Properties, and Preparation of Boronic Acid Derivatives": D. G. Hall in Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine (Ed.: D. G. Hall) Wiley-VCH, Weinheim, 2005, pp. 1-99.
  • 4
    • 0013319981 scopus 로고    scopus 로고
    • For a review on Pd-catalyzed coupling reactions of aryl chlorides, see
    • For a review on Pd-catalyzed coupling reactions of aryl chlorides, see: A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350;
    • (2002) Angew. Chem , vol.114 , pp. 4350
    • Littke, A.F.1    Fu, G.C.2
  • 5
    • 0037112673 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
    • (2002) Chem. Int. Ed , vol.41 , pp. 4176-4211
    • Angew1
  • 6
    • 1542637623 scopus 로고    scopus 로고
    • For reviews on transition-metal-catalyzed carbon-boron bond formation, see: a
    • For reviews on transition-metal-catalyzed carbon-boron bond formation, see: a) T. Ishiyama, N. Miyaura, Chem. Rec. 2004, 3, 271;
    • (2004) Chem. Rec , vol.3 , pp. 271
    • Ishiyama, T.1    Miyaura, N.2
  • 13
    • 34447538799 scopus 로고    scopus 로고
    • Although H2O is necessary for the borylation of 2-chloro-m-xylene (Table 2, entry 8) at 110°C to proceed to completion, an increased amount of reduced starting material is observed under these conditions. When the reaction of this substrate is conducted under the standard room-temperature conditions (Table 3, entry 5, catalyst decomposition (palladium black) is not observed, and a higher yield of the desired product is obtained
    • 2O is necessary for the borylation of 2-chloro-m-xylene (Table 2, entry 8) at 110°C to proceed to completion, an increased amount of reduced starting material is observed under these conditions. When the reaction of this substrate is conducted under the standard room-temperature conditions (Table 3, entry 5), catalyst decomposition (palladium black) is not observed, and a higher yield of the desired product is obtained.
  • 17
    • 4644300966 scopus 로고    scopus 로고
    • For a previous method for the preparation of symmetrical biaryl species via one-pot borylation and subsequent Suzuki-Miyaura reaction, see: C. F. Nising, U. K. Schmid, M. Nieger, S. Bräse, J. Org. Chem. 2004, 69, 6830
    • For a previous method for the preparation of symmetrical biaryl species via one-pot borylation and subsequent Suzuki-Miyaura reaction, see: C. F. Nising, U. K. Schmid, M. Nieger, S. Bräse, J. Org. Chem. 2004, 69, 6830.
  • 19
    • 34447513567 scopus 로고    scopus 로고
    • Gaussian 03, Revision D.01, M. J. Frisch et al., see the Supporting Information
    • Gaussian 03, Revision D.01, M. J. Frisch et al., see the Supporting Information
  • 24
    • 34447502828 scopus 로고    scopus 로고
    • Amine binding to a biaryl phosphine-PdII complex is substantially favored when the Pd center is distal to the non-phosphine-bearing ring of the ligand:, manuscript in preparation
    • II complex is substantially favored when the Pd center is distal to the non-phosphine-bearing ring of the ligand: T. E. Barder, M. R. Biscoe, S. L. Buchwald, manuscript in preparation.
    • Barder, T.E.1    Biscoe, M.R.2    Buchwald, S.L.3
  • 26
    • 34447558992 scopus 로고    scopus 로고
    • See the Supporting Information for details on the potential energy surface scan
    • See the Supporting Information for details on the potential energy surface scan.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.