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Volumn 353, Issue 2-3, 2011, Pages 309-314

Highly efficient suzuki-miyaura coupling of aryl tosylates and mesylates catalyzed by stable, cost-effective [1,3-bis(diphenylphosphino)propane] nickel(II) chloride [Ni(dppp)Cl2] with only 1amol% loading

Author keywords

aryl sulfonates; biaryls; boronic acids; nickel catalyst; Suzuki Miyaura coupling

Indexed keywords


EID: 79951818747     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000710     Document Type: Article
Times cited : (43)

References (55)
  • 1
    • 79951820774 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 5
    • 79951845069 scopus 로고    scopus 로고
    • For examples
    • For examples
  • 12
    • 79951819545 scopus 로고    scopus 로고
    • For reviews on using triflates as substrates, see
    • For reviews on using triflates as substrates, see
  • 13
    • 33751424969 scopus 로고    scopus 로고
    • references cited therein
    • Z. Gilson, R. Larock, Chem. Rev. 2006, 106, 4644, and references cited therein
    • (2006) Chem. Rev. , vol.106 , pp. 4644
    • Gilson, Z.1    Larock, R.2
  • 15
    • 79951844447 scopus 로고    scopus 로고
    • For some representative examples, see
    • For some representative examples, see
  • 25
    • 79951831282 scopus 로고    scopus 로고
    • For examples
    • For examples
  • 31
    • 79951820773 scopus 로고    scopus 로고
    • note
    • 2 (98%) used in this work is $61.80 per 50ag (Aldrich catalogue, 2009-2010).
  • 32
    • 79951829578 scopus 로고    scopus 로고
    • note
    • The cost for the several frequently used phosphine ligands in conventional cross-coupling of aryl chlorides, tosylates, and mesylates is 2-(di-tert-butylphosphino)biphenyl (JohnPhos, 97%) is $99.10 per gram; 2-di-tert-butylphosphino-2a-methylbiphenyl (t-BuMePhos, 97%) is $213.50 per gram; 2-di-tert-butylphosphino-2a,4a,6a-triisopropylbiphenyl (Xphos, 97%) is $99.10 per gram; however, bis(diphenylphosphino)propane (dppp, 97%) used in this work is ca. $20.10 per gram, which makes it one of the cheapest phosphine ligands in the chemical price list (Aldrich catalogue, 2009-2010).
  • 43
    • 79951828311 scopus 로고    scopus 로고
    • note
    • [6d]
  • 44
  • 46
    • 26144464085 scopus 로고
    • 2 (98%) was purchased from Stream Chemicals. Dppp ligands (>98%) was purchased from Shanghai Adamas Reagent Co. Ltd.
    • 2 (98%) was purchased from Stream Chemicals. Dppp ligands (>98%) was purchased from Shanghai Adamas Reagent Co. Ltd.
    • (1966) Inorg. Chem. , vol.5 , pp. 1968
    • Vanahecke, G.R.1    Horrocks Jr., W.D.2
  • 48
    • 79951836910 scopus 로고    scopus 로고
    • For examples
    • For examples
  • 55
    • 79951841391 scopus 로고    scopus 로고
    • note
    • It should be mentioned that, as an exceptional example, the cross-coupling of tosylate derivative of 3-N,N-dimethylphenol is somewhat sluggish, affording the biaryls in 57% average yield (Tablea2, entrya7). The reasons are not clear at this stage although the effect of several possible factors such as temperature, reaction time, and the purity of substrate were carefully examined.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.