메뉴 건너뛰기




Volumn 7, Issue 10, 2009, Pages 2155-2161

Trifluoromethyl-substituted pyridyl- and pyrazolylboronic acids and esters: Synthesis and Suzuki-Miyaura cross-coupling reactions

Author keywords

[No Author keywords available]

Indexed keywords

BORONATION; BUILDING BLOCK; COUPLING PRODUCT; CROSS-COUPLINGS; DRUG DISCOVERY; HOMOCOUPLING; LITHIATION; MATERIALS CHEMISTRY; MULTIRING; POTASSIUM FORMATE; PYRAZOLE; PYRAZOLES; PYRAZOLYL; PYRIDYL; SUZUKI-MIYAURA CROSS-COUPLING REACTION; TRIFLUOROMETHYL; X RAY CRYSTAL STRUCTURES;

EID: 67249104505     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b901024f     Document Type: Article
Times cited : (48)

References (86)
  • 1
    • 0003508266 scopus 로고    scopus 로고
    • Springer, Berlin, the shape and size of a compound;
    • For a general review of the biological and physical properties of organofluorine compounds see T. Hiyama, Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000. For examples where the replacement of a substituent, or addition of a trifluoromethyl group to a lead compound can alter
    • (2000) Organofluorine Compounds: Chemistry and Applications
    • Hiyama, T.1
  • 5
    • 4544316921 scopus 로고    scopus 로고
    • A SciFinder search (May 2008) for trifluoromethyl-substituted pyridines with biological activity gave >7500 results
    • J. C. Biffinger H. W. Kim S. G. DiMagno ChemBioChem. 2004 5 622
    • (2004) ChemBioChem. , vol.5 , pp. 622
    • Biffinger, J.C.1    Kim, H.W.2    Dimagno, S.G.3
  • 22
    • 0034703491 scopus 로고    scopus 로고
    • and references therein For trifluoromethyl-substituted benzenes via copper-mediated iodo/trifluoromethyl displacement see:
    • R. P. Singh J. M. Shreeve Tetrahedron 2000 56 7613
    • (2000) Tetrahedron , vol.56 , pp. 7613
    • Singh, R.P.1    Shreeve, J.M.2
  • 24
    • 0036156340 scopus 로고    scopus 로고
    • For a general review of trifluoromethyl-bearing aromatic and heterocyclic building blocks see:
    • F. Cottet M. Schlosser Eur. J. Org. Chem. 2002 327
    • (2002) Eur. J. Org. Chem. , pp. 327
    • Cottet, F.1    Schlosser, M.2
  • 35
    • 27644475970 scopus 로고    scopus 로고
    • D. G. Hall, (Ed.) Wiley-VCH, Weinheim, Germany, 123-170
    • A. Suzuki, in Boronic Acids, D. G. Hall, (Ed.) Wiley-VCH, Weinheim, Germany, 2005; Chapter 3, pp 123-170
    • (2005) Boronic Acids
    • Suzuki In, A.1
  • 39
    • 33745079610 scopus 로고    scopus 로고
    • A SciFinder search (May 2008) for commercially available bromo-(trifluoromethyl)-benzenes resulted in 704 compounds, for commercially available bromo-(trifluoromethyl)-pyridines resulted in 40 compounds. Commercially available chloro-(trifluoromethyl)-benzenes and -pyridines resulted in 26140 and 5246 compounds, respectively A SciFinder search (May 2008) for (trifluoromethyl)phenylboronic acids resulted in 71 commercially available compounds, from a number of suppliers, for example, Frontier Scientific, Apollo, Fluorochem and Sigma-Aldrich Examples of Suzuki-Miyaura cross-couplings of halo(trifluoromethyl)benzene derivatives;
    • J. S. Carey D. Laffan C. Thomson M. T. Williams Org. Biomol. Chem. 2006 4 2337
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 2337
    • Carey, J.S.1    Laffan, D.2    Thomson, C.3    Williams, M.T.4
  • 67
    • 67249085706 scopus 로고    scopus 로고
    • A SciFinder search (May 2008) for trifluoromethyl-substituted heterocyclic boronic acids and esters gave 49 results. Examples of pyridylboronic acid derivatives: F. Stauffer, and F. Pascal, PCT Int. Appl. WO2008012326, 2008
    • (2008) PCT Int. Appl. WO2008012326
    • Stauffer, F.1    Pascal, F.2
  • 77
    • 67249108756 scopus 로고    scopus 로고
    • 2007 reports the preparation of 4 and one example of a Suzuki-Miyaura cross-coupling reaction (with 3-bromo-l-methyl-l H -pyrazolo[3,4-d]pyrimidin-6- ylamine). The only analytical data given for 4 was the mass spectrum of its hydrochloride salt
    • I. Bruce, J. F. Hayler, G. C. Bloomfield, L. Edwards, B. Cox, and C. Howsham, PCT. Int., Appl. WO2007134828, 2007 reports the preparation of 4 and one example of a Suzuki-Miyaura cross-coupling reaction (with 3-bromo-l-methyl-l H -pyrazolo[3,4-d]pyrimidin-6-ylamine). The only analytical data given for 4 was the mass spectrum of its hydrochloride salt
    • (2007) PCT. Int., Appl. WO2007134828
    • Bruce, I.1    Hayler, J.F.2    Bloomfield, G.C.3    Edwards, L.4    Cox, B.5    Howsham, C.6
  • 80
    • 0001740992 scopus 로고
    • For examples of the lithiation of 3-(trifluoromethyl)pyrazole see:
    • R. G. Micetich Can. J. Chem. 1970 48 2006
    • (1970) Can. J. Chem. , vol.48 , pp. 2006
    • Micetich, R.G.1
  • 85
    • 0030857708 scopus 로고    scopus 로고
    • When the boron is attached to a carbon adjacent to a heteroatom the stability of the boronic acid is further decreased:
    • C. Coudret V. Mazenc Tetrahedron Lett. 1997 38 5293
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5293
    • Coudret, C.1    Mazenc, V.2
  • 86
    • 2342634252 scopus 로고    scopus 로고
    • and references therein. Pyrazolylboronic acids and esters are known to be prone to protodeboronation: Ref. 23c and 23e By-products obtained alongside product 52 were the product obtained from homo-coupling of the boronic acid, and debrominated compound 36 (which co-eluted during column chromatography), and unreacted starting material 50 (16%)
    • B. Abarca R. Ballesteros F. Blanco A. Bouillon V. Collot J.-R. Domínguez J.-C. Lancelot S. Rault Tetrahedron 2004 60 4887
    • (2004) Tetrahedron , vol.60 , pp. 4887
    • Abarca, B.1    Ballesteros, R.2    Blanco, F.3    Bouillon, A.4    Collot, V.5    Domínguez, J.-R.6    Lancelot, J.-C.7    Rault, S.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.