메뉴 건너뛰기




Volumn 39, Issue 12, 2009, Pages 2082-2092

Cu(OAc)2-catalyzed N-arylation of sulfonamides with arylboronic acids or trimethoxy(phenyl)silane

Author keywords

Arylboronic acids; Cu(OAc)2 catalyzed; sulfonamides; trimethoxy(phenyl)silane

Indexed keywords

BORONIC ACID DERIVATIVE; CARBON; COPPER DERIVATIVE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; SULFONAMIDE; TRIMETHOXY(PHENYL)SILANE; UNCLASSIFIED DRUG;

EID: 67650266899     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802638495     Document Type: Article
Times cited : (30)

References (28)
  • 6
    • 12344326693 scopus 로고    scopus 로고
    • Sulfonamide drugs binding to the colchicine site of tubulin: Thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry
    • (c) Banerjee, M.; Poddar, A.; Mitra, G.; Surolia, A.; Owa, T.; Bhattacharyya, B. Sulfonamide drugs binding to the colchicine site of tubulin: Thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry. J. Med. Chem. 2005, 48, 547-555.
    • (2005) J. Med. Chem , vol.48 , pp. 547-555
    • Banerjee, M.1    Poddar, A.2    Mitra, G.3    Surolia, A.4    Owa, T.5    Bhattacharyya, B.6
  • 7
    • 1942471653 scopus 로고    scopus 로고
    • Recent progress in copper-catalyzed cross- coupling reactions
    • (a) Deng, W.; Liu, L.; Guo, Q. X. Recent progress in copper-catalyzed cross- coupling reactions. Chin. J. Org. Chem. 2004, 24, 150-165
    • (2004) Chin. J. Org. Chem , vol.24 , pp. 150-165
    • Deng, W.1    Liu, L.2    Guo, Q.X.3
  • 8
    • 0346749657 scopus 로고    scopus 로고
    • Renaissance of Ullmann and Goldberg reactions- Progress in copper-catalyzed C-N, C-O, and C-S coupling
    • (b) Kunz, K.; Scholz, U.; Ganzer, D. Renaissance of Ullmann and Goldberg reactions- Progress in copper-catalyzed C-N, C-O, and C-S coupling. Synlett 2003, 2428-2439
    • (2003) Synlett , pp. 2428-2439
    • Kunz, K.1    Scholz, U.2    Ganzer, D.3
  • 9
    • 25444455340 scopus 로고    scopus 로고
    • Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by aminoacidligands
    • (c) Deng, W.; Liu, L.; Zhang, C.; Liu, M.; Guo, Q. X. Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by aminoacidligands. Tetrahedron Lett. 2005, 46, 7295-7298
    • (2005) Tetrahedron Lett , vol.46 , pp. 7295-7298
    • Deng, W.1    Liu, L.2    Zhang, C.3    Liu, M.4    Guo, Q.X.5
  • 10
    • 0037436943 scopus 로고    scopus 로고
    • Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating
    • (d) He, H.; Wu, Y. J. Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating. Tetrahedron Lett. 2003, 44, 3385-3386.
    • (2003) Tetrahedron Lett , vol.44 , pp. 3385-3386
    • He, H.1    Wu, Y.J.2
  • 11
    • 0035858723 scopus 로고    scopus 로고
    • Copper- catalyzed general C-N and C-O bond cross-coupling with arylboronic acid
    • Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Copper- catalyzed general C-N and C-O bond cross-coupling with arylboronic acid. Tetrahedron Lett. 2001, 42, 3415-3418.
    • (2001) Tetrahedron Lett , vol.42 , pp. 3415-3418
    • Lam, P.Y.S.1    Vincent, G.2    Clark, C.G.3    Deudon, S.4    Jadhav, P.K.5
  • 12
    • 3142671872 scopus 로고    scopus 로고
    • A simple copper salt catalyzed N-arylation of amines, amides, imides, and sulfonamides with arylboronic acids
    • Lan, J. B.; Zhang, G. L.; Yu, X. Q.; You, J. S.; Chen, L.; Yan, M.; Xie, R. G. A simple copper salt catalyzed N-arylation of amines, amides, imides, and sulfonamides with arylboronic acids. Synlett 2004, 1095-1097.
    • (2004) Synlett , pp. 1095-1097
    • Lan, J.B.1    Zhang, G.L.2    Yu, X.Q.3    You, J.S.4    Chen, L.5    Yan, M.6    Xie, R.G.7
  • 14
    • 0000121752 scopus 로고    scopus 로고
    • Cross-coupling reactions of aryl chlorides with organochlorosilanes: Highly effective methods for arylation or alkenylation of aryl chlorides
    • (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. Cross-coupling reactions of aryl chlorides with organochlorosilanes: Highly effective methods for arylation or alkenylation of aryl chlorides. J. Org. Chem. 1996, 61, 7232-7233
    • (1996) J. Org. Chem , vol.61 , pp. 7232-7233
    • Gouda, K.1    Hagiwara, E.2    Hatanaka, Y.3    Hiyama, T.4
  • 15
    • 0001443339 scopus 로고    scopus 로고
    • Utilization of tetrabutylammo- nium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage
    • (b) Pilcher, A. S.; DeShong, P. Utilization of tetrabutylammo- nium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage. J. Org. Chem. 1996, 61, 6901-6905
    • (1996) J. Org. Chem , vol.61 , pp. 6901-6905
    • Pilcher, A.S.1    DeShong, P.2
  • 16
    • 0033617214 scopus 로고    scopus 로고
    • Synthesis of unsymmetrical biaryls by palladium-catalyzed cross coupling reactions of arenes with tetrabutylammonium triphenyldifluorosilicate, a hypervalent silicon reagent
    • (c) Mowery, M. E.; DeShong, P. Synthesis of unsymmetrical biaryls by palladium-catalyzed cross coupling reactions of arenes with tetrabutylammonium triphenyldifluorosilicate, a hypervalent silicon reagent. J. Org. Chem. 1999, 64, 3266-3270
    • (1999) J. Org. Chem , vol.64 , pp. 3266-3270
    • Mowery, M.E.1    DeShong, P.2
  • 17
    • 0000831654 scopus 로고    scopus 로고
    • Synthesis of unsymmetrical biaryls from arylsilacyclobutanes
    • (d) Denmark, S. E.; Wu, Z. Synthesis of unsymmetrical biaryls from arylsilacyclobutanes. Org. Lett. 1999, 1, 1495-1498
    • (1999) Org. Lett , vol.1 , pp. 1495-1498
    • Denmark, S.E.1    Wu, Z.2
  • 18
    • 28344443526 scopus 로고    scopus 로고
    • 2/DABCO as an inexpensive and efficient catalytic system for Hiyama cross-coupling reactions of aryl halides with aryltrimethoxysi- lanes
    • 2/DABCO as an inexpensive and efficient catalytic system for Hiyama cross-coupling reactions of aryl halides with aryltrimethoxysi- lanes. Synthesis 2005, 3039-3044
    • (2005) Synthesis , pp. 3039-3044
    • Li, J.H.1    Deng, C.L.2    Liu, W.J.3    Xie, Y.X.4
  • 19
    • 33645373308 scopus 로고    scopus 로고
    • Improved procedure for palladium-catalyzed Hiyama cross-coupling reaction of aryl halides with aryltrimethoxysilanes under solvent-free conditions
    • (f) Li, J. H.; Deng, C. L.; Xie, Y. X. Improved procedure for palladium-catalyzed Hiyama cross-coupling reaction of aryl halides with aryltrimethoxysilanes under solvent-free conditions. Synthesis 2006, 969-974
    • (2006) Synthesis , pp. 969-974
    • Li, J.H.1    Deng, C.L.2    Xie, Y.X.3
  • 20
    • 33845522428 scopus 로고    scopus 로고
    • Palladium-catalyzed Sonogashira and Hiyama reactions using phosphine-free hydrazone ligands
    • (g) Mino, T.; Shirae, Y.; Saito, T.; Sakamoto, M.; Fujita, T. Palladium-catalyzed Sonogashira and Hiyama reactions using phosphine-free hydrazone ligands. J. Org. Chem. 2006, 71, 9499-9502
    • (2006) J. Org. Chem , vol.71 , pp. 9499-9502
    • Mino, T.1    Shirae, Y.2    Saito, T.3    Sakamoto, M.4    Fujita, T.5
  • 21
    • 34547094802 scopus 로고    scopus 로고
    • 2-catalyzed fluoride-free cross-coupling reactions of arylsiloxanes with aryl bromides in aqueous medium
    • 2-catalyzed fluoride-free cross-coupling reactions of arylsiloxanes with aryl bromides in aqueous medium. J. Org. Chem. 2007, 72, 5927-5930.
    • (2007) J. Org. Chem , vol.72 , pp. 5927-5930
    • Shi, S.Y.1    Zhang, Y.H.2
  • 22
    • 0042835757 scopus 로고    scopus 로고
    • Photo-Fries rearrangement of N-arylsulfona- mides to aminoaryl sulfone derivatives
    • Park, K. K.; Lee, J. J.; Ryu, J. Photo-Fries rearrangement of N-arylsulfona- mides to aminoaryl sulfone derivatives. Tetrahedron 2003, 59, 7651-7659.
    • (2003) Tetrahedron , vol.59 , pp. 7651-7659
    • Park, K.K.1    Lee, J.J.2    Ryu, J.3
  • 24
    • 67650249360 scopus 로고    scopus 로고
    • Preparation of
    • N-phenylbenzenesulfonamide derivatives as insecticides, miticides, and nematocides. WO Patent 9700857, 1997; Chem. Abstr. 1997,126, 143975
    • Hirohumi, N.; Satoshi, G.; Keizaburo, M.; Seiichi, W.; Hilsashi, T. Preparation of N-phenylbenzenesulfonamide derivatives as insecticides, miticides, and nematocides. WO Patent 9700857, 1997; Chem. Abstr. 1997,126, 143975.
    • Hirohumi, N.1    Satoshi, G.2    Keizaburo, M.3    Seiichi, W.4    Hilsashi, T.5
  • 26
    • 9644307847 scopus 로고    scopus 로고
    • a vis-à-vis physiological activity of sulfonamides: A dominating role of surface tension (inverse steric parameter)
    • a vis-à-vis physiological activity of sulfonamides: A dominating role of surface tension (inverse steric parameter). Bioorg. Med. Chem. Lett. 2005, 15, 203-209.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 203-209
    • Thakur, M.1    Thakur, A.2    Khadikarc, P.V.3    Supurand, C.T.4
  • 28
    • 7444225806 scopus 로고    scopus 로고
    • Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base
    • Sharma, A. K.; Das, S. K. Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base. Synth. Commun. 2004, 34, 3807-3819.
    • (2004) Synth. Commun , vol.34 , pp. 3807-3819
    • Sharma, A.K.1    Das, S.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.