메뉴 건너뛰기




Volumn 132, Issue 40, 2010, Pages 14073-14075

A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CHLORIDE; BASIC CONDITIONS; BORONIC ACID; CATALYTICALLY ACTIVE SPECIES; COUPLING PROCESS; MONODENTATES; PRECATALYSTS; ROOM TEMPERATURE; SHORT REACTION TIME; SUZUKI-MIYAURA COUPLING REACTION; SUZUKI-MIYAURA REACTION; TRIFLATES;

EID: 77957698670     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1073799     Document Type: Article
Times cited : (525)

References (47)
  • 4
    • 0001480580 scopus 로고
    • Both base- and metal-catalyzed deboronation of boronic acids may occur under typical SMC reactions
    • Both base- and metal-catalyzed deboronation of boronic acids may occur under typical SMC reactions. Kuivila, H. G., Reuwer, J. F., and Mangravite, J. A. Can. J. Chem. 1963, 41, 3081
    • (1963) Can. J. Chem. , vol.41 , pp. 3081
    • Kuivila, H.G.1    Reuwer, J.F.2    Mangravite, J.A.3
  • 6
    • 77957700097 scopus 로고    scopus 로고
    • While 2,3- and 2,4-difluorophenylboronic acids could be coupled using ligand SPhos at 80-90 °C, these conditions did not allow the efficient coupling of 1 or 2
    • While 2,3- and 2,4-difluorophenylboronic acids could be coupled using ligand SPhos at 80-90 °C, these conditions did not allow the efficient coupling of 1 or 2
  • 8
    • 77957703524 scopus 로고    scopus 로고
    • For some examples for the coupling of 2,6-difluorophenylboronic acid with vinyl triflates and aryl bromides, see
    • For some examples for the coupling of 2,6-difluorophenylboronic acid with vinyl triflates and aryl bromides, see
  • 16
    • 77957702874 scopus 로고    scopus 로고
    • For some representative examples of the coupling of five-membered 2-heteroaromatic boronic acids, see
    • For some representative examples of the coupling of five-membered 2-heteroaromatic boronic acids, see
  • 23
    • 77957695778 scopus 로고    scopus 로고
    • 2-heterocyclic MIDA boronates were successfully employed for SMCs (see ref 4a), but polyfluorophenyl MIDA boronates were not described. MIDA = N -methyliminodiacetic acid
    • 2-heterocyclic MIDA boronates were successfully employed for SMCs (see ref 4a), but polyfluorophenyl MIDA boronates were not described. MIDA = N -methyliminodiacetic acid.
  • 25
    • 77957700620 scopus 로고    scopus 로고
    • 3K salts were coupled to 4-bromobenzonitrile
    • 3K salts were coupled to 4-bromobenzonitrile
  • 27
    • 77957719316 scopus 로고    scopus 로고
    • 3K salts
    • 3K salts
  • 29
    • 77957690997 scopus 로고    scopus 로고
    • 3K salts to the free boronic acid likely occurs prior to cross-coupling
    • 3K salts to the free boronic acid likely occurs prior to cross-coupling
  • 34
    • 77957690828 scopus 로고    scopus 로고
    • It should be mentioned that with copper or palladium catalysts, aryl bromides and chlorides can be directly coupled to polyfluorobenzenes via C-H activation processes, but high temperatures and long reaction times are required
    • It should be mentioned that with copper or palladium catalysts, aryl bromides and chlorides can be directly coupled to polyfluorobenzenes via C-H activation processes, but high temperatures and long reaction times are required.
  • 38
    • 77957701173 scopus 로고    scopus 로고
    • The reductive elimination of 4-methoxy-2′,6′-difluorobiphenyl from an isolated Pd(II) complex has been reported
    • The reductive elimination of 4-methoxy-2′,6′-difluorobiphenyl from an isolated Pd(II) complex has been reported
  • 42
    • 77957691172 scopus 로고    scopus 로고
    • -
    • -.
  • 43
    • 77957708140 scopus 로고    scopus 로고
    • 2O/pyridine mixture at elevated temperatures were reported
    • 2O/pyridine mixture at elevated temperatures were reported
  • 45
    • 77957699042 scopus 로고    scopus 로고
    • 4 solution prior to addition of the precatalyst and aryl chloride, and we found the same ratio of products as before
    • 4 solution prior to addition of the precatalyst and aryl chloride, and we found the same ratio of products as before.
  • 46
    • 77957717643 scopus 로고    scopus 로고
    • The attempted coupling of 2,3,6-trifluorophenylboronic acid with 4-chloroacetophenone under microwave irradiation led exclusively to the deboronated compound, trifluorobenzene
    • The attempted coupling of 2,3,6-trifluorophenylboronic acid with 4-chloroacetophenone under microwave irradiation led exclusively to the deboronated compound, trifluorobenzene


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.