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Volumn 64, Issue 18, 1999, Pages 6797-6803

Palladium/P,O-ligand-catalyzed suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; BROMIDE; CHLORIDE; IODIDE; LIGAND; PALLADIUM COMPLEX;

EID: 0032887312     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990805t     Document Type: Article
Times cited : (234)

References (76)
  • 7
    • 84947151032 scopus 로고
    • Leading references for Suzuki reactions involving aryl iodides and bromides: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519.
    • (1981) Synth. Commun. , vol.11 , pp. 513-519
    • Miyaura, N.1    Yanagi, T.2    Suzuki, A.3
  • 20
    • 0011806674 scopus 로고
    • Leading references for Suzuki reactions involving aryl triflates: (a) Oh-e, T.; Miyaura, N.; Suzuki, A. Synlett 1990, 221-223.
    • (1990) Synlett , pp. 221-223
    • Oh-e, T.1    Miyaura, N.2    Suzuki, A.3
  • 44
  • 45
    • 0000728442 scopus 로고    scopus 로고
    • Ni-catalyzed Suzuki reactions involving aryl chlorides; see ref 6f. See also: (a) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024-8030.
    • (1997) J. Org. Chem. , vol.62 , pp. 8024-8030
    • Saito, S.1    Oh-Tani, S.2    Miyaura, N.3
  • 56
    • 0344197279 scopus 로고    scopus 로고
    • note
    • The synthesis and characterization of ligand 1 was described previously; see ref 12a. For general utility of ligand 1 in palladium/ ligand-catalyzed animation of aryl chlorides, see ref 12a,b.
  • 57
    • 0345491157 scopus 로고    scopus 로고
    • note
    • 2/ligand 2-catalyzed reaction of 5-chloro-m-xylene with N-heptylmethylamine under our standard aryl animation conditions proceeded to completion overnight to afford the desired arylamine product.
  • 58
    • 0344629002 scopus 로고    scopus 로고
    • note
    • 2 as the metal precursor, other suitable Pd(0) or Pd(II) metal complexes could also be used. A variety of different metal complexes have been employed as catalyst precursors or catalysts for Suzuki reactions; see ref 1. Also, while most of our studies utilized a Pd/L ratio of 1/3, Pd/L ratios of 1/1-1.5 are also generally suitable under rigorously air-free conditions.
  • 61
    • 0344629001 scopus 로고    scopus 로고
    • note
    • 6): δ - 8.3.
  • 62
    • 37049068274 scopus 로고
    • The Pd-O bond distance in complex 14 compares favorably with the Pd-O covalent bond distances reported for square planar complexes (2.0-2.16 Å) and is similar to the Pd-O bond distance of the previously characterized complex 12 (2.16 Å); see ref 12a. See also: (a) Kiers, N. H.; Feringa, B. L.; Kooijman, H.; Spek, A. L.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1169-1170.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 1169-1170
    • Kiers, N.H.1    Feringa, B.L.2    Kooijman, H.3    Spek, A.L.4    Van Leeuwen, P.W.N.M.5
  • 64
    • 3743092578 scopus 로고
    • and references therein
    • (c) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163-1188 and references therein.
    • (1988) Chem. Rev. , vol.88 , pp. 1163-1188
    • Bryndza, H.E.1    Tam, W.2
  • 66
    • 0344197277 scopus 로고    scopus 로고
    • note
    • 31P NMR spectra of the reaction mixture exhibited significantly broad resonances.
  • 71
    • 0344197276 scopus 로고    scopus 로고
    • note
    • 3P ligand presumably are sufficient for the generation and involvement of the most desired mono-phosphine "LPd" intermediates. Alternatively, the desired monophosphine "LPd" intermediates could also be accessible because of steric and electronic properties of certain aryl halide substrates and reaction conditions.
  • 74
    • 0345491156 scopus 로고    scopus 로고
    • Commercially available
    • Commercially available.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.