메뉴 건너뛰기




Volumn 6, Issue 6, 2003, Pages 876-883

Synthetic applications of palladium-catalyzed hydroarylation and related systems

Author keywords

Alkenes; Alkynes; Asymmetric synthesis; Carbon carbon bond formation; Hydroarylation; Palladium catalyzed; Regiochemistry; Stereochemistry; Synthetic applications

Indexed keywords

ALKALOID DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ANTIVIRUS AGENT; ARGEMONINE; EPIBATIDINE; NATURAL PRODUCT; PALLADIUM; RETINOIC ACID RECEPTOR; RETINOID X RECEPTOR; STEROID; TACHYKININ RECEPTOR ANTAGONIST; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0347719511     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review
Times cited : (19)

References (27)
  • 1
    • 0037782994 scopus 로고    scopus 로고
    • Palladium-catalyzed coupling of organyl halides to alkenes - The Heck reaction
    • Diederich F, Stang PJ (Eds), Wiley-VCH, Weiheim, Germany
    • Brase S, de Meijere A: Palladium-catalyzed coupling of organyl halides to alkenes - The Heck reaction. In: Metal-Catalyzed Cross-Coupling Reactions. Diederich F, Stang PJ (Eds), Wiley-VCH, Weiheim, Germany (1998):99-166.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 99-166
    • Brase, S.1    De Meijere, A.2
  • 2
    • 0001325299 scopus 로고    scopus 로고
    • Palladium-catalyzed olefinations of aryl halides (Heck reaction) and related transformations
    • Building Blocks and Fine Chemicals. Beller M, Bolm C (Eds), Wiley-VCH, Weinheim, Germany
    • Beller M, Riermeier TH, Stark G: Palladium-catalyzed olefinations of aryl halides (Heck reaction) and related transformations. In: Transition Metals for Organic Synthesis; Building Blocks and Fine Chemicals. Beller M, Bolm C (Eds), Wiley-VCH, Weinheim, Germany (1998) 1:208-236.
    • (1998) Transition Metals for Organic Synthesis , vol.1 , pp. 208-236
    • Beller, M.1    Riermeier, T.H.2    Stark, G.3
  • 3
    • 0034249671 scopus 로고    scopus 로고
    • The Heck reaction as a sharpening stone of palladium catalysis
    • Beletskaya IP, Cheprakov AV: The Heck reaction as a sharpening stone of palladium catalysis. Chem Rev (2000) 100(8):3009-3066. A current view of the Heck reaction.
    • (2000) Chem Rev , vol.100 , Issue.8 , pp. 3009-3066
    • Beletskaya, I.P.1    Cheprakov, A.V.2
  • 4
    • 0000470387 scopus 로고
    • The palladium-catalyzed reaction of aryl iodides with mono and disubstituted acetylenes: A new synthesis of trisubstituted alkenes
    • Cacchi S, Felici M, Pietroni B: The palladium-catalyzed reaction of aryl iodides with mono and disubstituted acetylenes: A new synthesis of trisubstituted alkenes. Tetrahedron Lett (1984) 25(29):3137-3140. The mechanism of Pd-catalyzed hydroarylation reaction is proposed.
    • (1984) Tetrahedron Lett , vol.25 , Issue.29 , pp. 3137-3140
    • Cacchi, S.1    Felici, M.2    Pietroni, B.3
  • 5
    • 0001848413 scopus 로고    scopus 로고
    • Heterocycles via cyclization of alkynes promoted by organopalladium complexes
    • Cacchi S: Heterocycles via cyclization of alkynes promoted by organopalladium complexes. J Organomet Chem (1999) 576(1-2):42-46. A comprehensive review on Pd-catalyzed hydroarylation/cyclization of alkynes and cyclization of alkynes containing proximate nucleophiles.
    • (1999) J Organomet Chem , vol.576 , Issue.1-2 , pp. 42-46
    • Cacchi, S.1
  • 6
    • 0030598028 scopus 로고    scopus 로고
    • Palladium-catalyzed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines
    • Cacchi S, Fabrizi G, Marinelli F, Moro L, Pace P: Palladium-catalyzed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines. Tetrahedron (1996) 52(30):10225-10240.
    • (1996) Tetrahedron , vol.52 , Issue.30 , pp. 10225-10240
    • Cacchi, S.1    Fabrizi, G.2    Marinelli, F.3    Moro, L.4    Pace, P.5
  • 7
    • 0030865159 scopus 로고    scopus 로고
    • A regio- and stereocontrolled method for preparing 3,3-diaryacrylamides
    • Hay LA, Mitchell D: A regio- and stereocontrolled method for preparing 3,3-diaryacrylamides. Tetrahedron Lett (1997) 38(37):6533-6536.
    • (1997) Tetrahedron Lett , vol.38 , Issue.37 , pp. 6533-6536
    • Hay, L.A.1    Mitchell, D.2
  • 8
    • 0031868270 scopus 로고    scopus 로고
    • Palladium-catalyzed hydroarylation of propiolamides. A regio- and stereocontrolled method for preparing 3,3-diarylacrylamides
    • Hay LA, Koenig TM, Ginah FO, Copp JD, Mitchell, D: Palladium-catalyzed hydroarylation of propiolamides. A regio- and stereocontrolled method for preparing 3,3-diarylacrylamides. J Org Chem (1998) 63(15):5050-5058. A detailed description of the preparation of 3,3-diarylacrylamides based on a regio- and stereoselective hydroarylation strategy.
    • (1998) J Org Chem , vol.63 , Issue.15 , pp. 5050-5058
    • Hay, L.A.1    Koenig, T.M.2    Ginah, F.O.3    Copp, J.D.4    Mitchell, D.5
  • 9
    • 9644285669 scopus 로고
    • A convient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines
    • Sonongashira K, Tohda Y, Hagihara N: A convient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett (1975) 16(50):4467-4470.
    • (1975) Tetrahedron Lett , vol.16 , Issue.50 , pp. 4467-4470
    • Sonongashira, K.1    Tohda, Y.2    Hagihara, N.3
  • 10
    • 0001713537 scopus 로고
    • Palladium-catalysed stereoselective hydrovinylation of disubstituted acetylenes: Preparation of functionalized 1,2,4-trisubstituted-1,3-dienes
    • Arcadi A, Bernocchi E, Burini A, Cacchi S, Marinelli F, Pietroni B: Palladium-catalysed stereoselective hydrovinylation of disubstituted acetylenes: Preparation of functionalized 1,2,4-trisubstituted-1,3-dienes. Tetrahedron Lett (1989) 30(26):3465-3468.
    • (1989) Tetrahedron Lett , vol.30 , Issue.26 , pp. 3465-3468
    • Arcadi, A.1    Bernocchi, E.2    Burini, A.3    Cacchi, S.4    Marinelli, F.5    Pietroni, B.6
  • 12
    • 0002165840 scopus 로고    scopus 로고
    • The palladium-catalysed arylation and vinylation of alkenes-enantioselective fashion
    • Shibasaki M, Vogl EM: The palladium-catalysed arylation and vinylation of alkenes-enantioselective fashion. J Organomet Chem (1999) 576(1-2):1-15.
    • (1999) J Organomet Chem , vol.576 , Issue.1-2 , pp. 1-15
    • Shibasaki, M.1    Vogl, E.M.2
  • 13
    • 0026351422 scopus 로고
    • Asymmetric catalysis. 72. Enantioselective hydroarylation of norbornene and norbornadiene with palladium (11) acetate/phosphine catalysts
    • Brunner H, Kramler K: Asymmetric catalysis. 72. Enantioselective hydroarylation of norbornene and norbornadiene with palladium (11) acetate/phosphine catalysts. Synthesis (1991) (12):1121-1124.
    • (1991) Synthesis , Issue.12 , pp. 1121-1124
    • Brunner, H.1    Kramler, K.2
  • 14
    • 70649095635 scopus 로고
    • Asymmetric Heck-type hydroarylation of norbornene with phenyl triflate catalyzed by palladium complexes of chiral (β -N-sulfonylaminoalkyl)-phosphines
    • Sakuraba S, Awano K, Achiwa K: Asymmetric Heck-type hydroarylation of norbornene with phenyl triflate catalyzed by palladium complexes of chiral (β-N-sulfonylaminoalkyl)-phosphines. Synlett (1994) (4):291-292.
    • (1994) Synlett , Issue.4 , pp. 291-292
    • Sakuraba, S.1    Awano, K.2    Achiwa, K.3
  • 15
    • 0034616253 scopus 로고    scopus 로고
    • Enantioselective Heck-type hydroarylation of norbornene with phenyl iodide catalyzed by palladium/quinolinyl-oxazolines
    • Wu X-Y, Xu H-D, Zhou Q-L, Chan ASC: Enantioselective Heck-type hydroarylation of norbornene with phenyl iodide catalyzed by palladium/quinolinyl-oxazolines. Tetrahedron Asymmetry (2000) 11(6):1255-1257.
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.6 , pp. 1255-1257
    • Wu, X.-Y.1    Xu, H.-D.2    Zhou, Q.-L.3    Chan, A.S.C.4
  • 16
    • 0034595666 scopus 로고    scopus 로고
    • Highly efficient phosphapalladacyclic catalysts for the hydroarylation of norbornene
    • Brunel JM, Heumann A, Buono G: Highly efficient phosphapalladacyclic catalysts for the hydroarylation of norbornene. Angew Chem Int Ed (2000) 39(11):1946-1949.
    • (2000) Angew Chem Int Ed , vol.39 , Issue.11 , pp. 1946-1949
    • Brunel, J.M.1    Heumann, A.2    Buono, G.3
  • 17
    • 0001308940 scopus 로고    scopus 로고
    • Palladium-Duphos structural and enantioselective hydroarylation chemistry
    • Drago D, Pregosin PS: Palladium-Duphos structural and enantioselective hydroarylation chemistry. Organometallics (2002) 21(6):1208-1215.
    • (2002) Organometallics , vol.21 , Issue.6 , pp. 1208-1215
    • Drago, D.1    Pregosin, P.S.2
  • 18
    • 0026551490 scopus 로고
    • Epibatidine: A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog
    • Spande TF, Garaffo HM, Edwards MW, Yeh HJ, Pannell L, Daly JW: Epibatidine: A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog. J Am Chem Soc (1992) 114(9):3475-3478.
    • (1992) J Am Chem Soc , vol.114 , Issue.9 , pp. 3475-3478
    • Spande, T.F.1    Garaffo, H.M.2    Edwards, M.W.3    Yeh, H.J.4    Pannell, L.5    Daly, J.W.6
  • 19
    • 0032500164 scopus 로고    scopus 로고
    • Regiochemistry of the reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene. Synthesis of epibatidine analogues
    • Kasyan A, Wagner C, Maier ME: Regiochemistry of the reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene. Synthesis of epibatidine analogues. Tetrahedron (1998) 54(28):8047-8054.
    • (1998) Tetrahedron , vol.54 , Issue.28 , pp. 8047-8054
    • Kasyan, A.1    Wagner, C.2    Maier, M.E.3
  • 20
    • 0029975474 scopus 로고    scopus 로고
    • Synthesis of epibatidine homologues: Homoepibatidine and bis-homoepibatidine
    • Malpass JR, Hemmings DA, Wallis AL: Synthesis of epibatidine homologues: Homoepibatidine and bis-homoepibatidine. Tetrahedron Lett (1996) 37(22):3911-3914.
    • (1996) Tetrahedron Lett , vol.37 , Issue.22 , pp. 3911-3914
    • Malpass, J.R.1    Hemmings, D.A.2    Wallis, A.L.3
  • 21
    • 0029921266 scopus 로고    scopus 로고
    • Synthesis of new TNF-α inhibitors and their biological properties
    • Fujiwara N, Ueda Y, Ohashi N: Synthesis of new TNF-α inhibitors and their biological properties. Bioorg Med Chem Lett (1996) 6(7):743-748.
    • (1996) Bioorg Med Chem Lett , vol.6 , Issue.7 , pp. 743-748
    • Fujiwara, N.1    Ueda, Y.2    Ohashi, N.3
  • 22
    • 0035847489 scopus 로고    scopus 로고
    • An efficient synthesis of argemonine, a pavine alkaloid
    • Ruchirawat S, Namsa-aid A: An efficient synthesis of argemonine, a pavine alkaloid. Tetrahedron Lett (2001) 42(7):1359-1361.
    • (2001) Tetrahedron Lett , vol.42 , Issue.7 , pp. 1359-1361
    • Ruchirawat, S.1    Namsa-Aid, A.2
  • 24
    • 0032580391 scopus 로고    scopus 로고
    • New synthetic retinoids obtained by palladium-catalyzed tandem cyclization-hydride capture process
    • Diaz P, Gendre F, Stella L, Charpentier B: New synthetic retinoids obtained by palladium-catalyzed tandem cyclization-hydride capture process. Tetrahedron (1998) 54(18):4579-4590.
    • (1998) Tetrahedron , vol.54 , Issue.18 , pp. 4579-4590
    • Diaz, P.1    Gendre, F.2    Stella, L.3    Charpentier, B.4
  • 25
    • 0032228128 scopus 로고    scopus 로고
    • Neurokinin receptor antagonists
    • Ellis GP, Luscombe DK, Oxford AW (Eds), Elsevier Sciences BV, Amsterdam, the Netherlands
    • Swain CJ: Neurokinin receptor antagonists. In: Progress in Medicinal Chemistry. Ellis GP, Luscombe DK, Oxford AW (Eds), Elsevier Sciences BV, Amsterdam, the Netherlands (1998) 35.
    • (1998) Progress in Medicinal Chemistry , pp. 35
    • Swain, C.J.1
  • 26
    • 0035826346 scopus 로고    scopus 로고
    • Stereocontrolled syntheses of epimeric 3-aryl-6-phenyl-1-oxa-7-azaspiro[4.5]decane NK-1 receptor antagonist precursors
    • 1 receptor antagonist precursor with high regio-and stereocontrol is described.
    • (2001) Org Lett , vol.3 , Issue.5 , pp. 667-670
    • Kulagowski, J.J.1    Curtis, N.R.2    Swain, C.J.3    Williams, B.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.