메뉴 건너뛰기




Volumn 21, Issue 26, 2015, Pages 9550-9555

Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides

Author keywords

acid chloride; carbonylation; mechanism; palladium; reductive elimination

Indexed keywords

CARBON; CARBONYLATION; CATALYSIS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; LIGANDS; MECHANISMS; METAL HALIDES; PALLADIUM; PHOSPHORUS COMPOUNDS;

EID: 84934933946     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500476     Document Type: Article
Times cited : (43)

References (68)
  • 11
    • 84934975429 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 10829
    • (2013) Angew. Chem. , vol.125 , pp. 10829
  • 13
    • 84934960869 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 10008
    • (2012) Angew. Chem. , vol.124 , pp. 10008
  • 16
    • 84934949487 scopus 로고    scopus 로고
    • 2e
    • 2e Angew. Chem. 2011, 123, 6465
    • (2011) Angew. Chem. , vol.123 , pp. 6465
  • 20
    • 84934992323 scopus 로고    scopus 로고
    • 2h
    • 2h Angew. Chem. 2010, 122, 3410
    • (2010) Angew. Chem. , vol.122 , pp. 3410
  • 33
    • 0344697933 scopus 로고
    • PhCO-Cl BDE:, for other sources
    • PhCO-Cl BDE:, M. Szwarc, J. W. Taylor, J. Chem. Phys. 1954, 22, 270; for other sources
    • (1954) J. Chem. Phys. , vol.22 , pp. 270
    • Szwarc, M.1    Taylor, J.W.2
  • 35
    • 42949084685 scopus 로고    scopus 로고
    • While the rate constant for PhBr oxidative addition to Pd(PtBu3)2 is not known due to complications of product decomposition, the half-life of this reaction is approximately 6.5h at 70C, relative to ca. 10min for PhCOCl at 25C. Conversely, PhI oxidative addition rates suggest an approximate half-life of 25min in neat PhI at 25C
    • While the rate constant for PhBr oxidative addition to Pd(PtBu3)2 is not known due to complications of product decomposition, the half-life of this reaction is approximately 6.5h at 70C (, F. Barrios-Landeros, B. P. Carrow, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 5842), relative to ca. 10min for PhCOCl at 25C. Conversely, PhI oxidative addition rates suggest an approximate half-life of 25min in neat PhI at 25C
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 5842
    • Barrios-Landeros, F.1    Carrow, B.P.2    Hartwig, J.F.3
  • 39
    • 85053398349 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 9110
    • (2011) Angew. Chem. , vol.123 , pp. 9110
  • 45
    • 33244456583 scopus 로고    scopus 로고
    • for a computational study of the role of palladium electronics on C£X reductive elimination
    • N. M. West, S. Reinartz, P. S. White, J. L. Templeton, J. Am. Chem. Soc. 2006, 128, 2059; for a computational study of the role of palladium electronics on C£X reductive elimination
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2059
    • West, N.M.1    Reinartz, S.2    White, P.S.3    Templeton, J.L.4
  • 52
    • 70350254143 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 4176.
    • (2009) Angew. Chem. , vol.121 , pp. 4176
  • 53
    • 84934939343 scopus 로고    scopus 로고
    • For alternative approaches to expanding the scope of carbonylations, see
    • For alternative approaches to expanding the scope of carbonylations, see
  • 59
    • 84934991616 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 8868.
    • (2010) Angew. Chem. , vol.122 , pp. 8868
  • 60
    • 84934934735 scopus 로고    scopus 로고
    • We are aware of only one report of hydrazine in carbonylative coupling, and this required high Pd loading (30mol%), 150C, and was performed on a 2-3mg scale
    • We are aware of only one report of hydrazine in carbonylative coupling, and this required high Pd loading (30mol%), 150C, and was performed on a 2-3mg scale
  • 63
    • 84934892967 scopus 로고    scopus 로고
    • Examples of the reaction of hydrazine with carbonylated products
    • Examples of the reaction of hydrazine with carbonylated products
  • 66
    • 80052600542 scopus 로고    scopus 로고
    • for an alternative use of reactive nitrogen nucleophiles in carbonylation, see
    • Angew. Chem. 2010, 122, 335; for an alternative use of reactive nitrogen nucleophiles in carbonylation, see
    • (2010) Angew. Chem. , vol.122 , pp. 335
  • 68
    • 84934906557 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 3728.
    • (2012) Angew. Chem. , vol.124 , pp. 3728


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.