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Volumn 8, Issue , 2012, Pages 1730-1746

Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes

Author keywords

Alkenylation; Arylation; C H functionalization; Indoles; N H functionalization; Pd catalysis

Indexed keywords


EID: 84867828492     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.8.198     Document Type: Review
Times cited : (86)

References (86)
  • 1
    • 33947493717 scopus 로고    scopus 로고
    • Organometallic chemistry: C-H activation
    • DOI 10.1038/446391a, PII 446391A
    • Bergman, R. G. Nature 2007, 446, 391-393. doi:10.1038/446391a (Pubitemid 46474593)
    • (2007) Nature , vol.446 , Issue.7134 , pp. 391-393
    • Bergman, R.G.1
  • 2
    • 68949141616 scopus 로고    scopus 로고
    • doi:10.1039/b907743j
    • Chemler, S. R. Org. Biomol. Chem. 2009, 7, 3009-3019. doi:10.1039/b907743j
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 3009-3019
    • Chemler, S.R.1
  • 4
    • 0036589261 scopus 로고    scopus 로고
    • Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects
    • DOI 10.1021/cr0104330
    • Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770. doi:10.1021/cr0104330 (Pubitemid 35377653)
    • (2002) Chemical Reviews , vol.102 , Issue.5 , pp. 1731-1769
    • Ritleng, V.1    Sirlin, C.2    Pfeffer, M.3
  • 5
    • 80053899534 scopus 로고    scopus 로고
    • doi:10.1055/s-0030-1260212
    • Nakao, Y. Synthesis 2011, 3209-3219. doi:10.1055/s-0030-1260212
    • (2011) Synthesis , pp. 3209-3219
    • Nakao, Y.1
  • 6
    • 84859742675 scopus 로고    scopus 로고
    • doi:10.1039/c2cs15281a
    • Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651-3678. doi:10.1039/c2cs15281a
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 3651-3678
    • Song, G.1    Wang, F.2    Li, X.3
  • 7
    • 79951648236 scopus 로고    scopus 로고
    • doi:10.1021/ar1000764
    • Nolan, S. P. Acc. Chem. Res. 2011, 44, 91-100. doi:10.1021/ar1000764
    • (2011) Acc. Chem. Res. , vol.44 , pp. 91-100
    • Nolan, S.P.1
  • 8
    • 70350608170 scopus 로고    scopus 로고
    • doi:10.1002/adsc.200900426
    • Zhang, M. Adv. Synth. Catal. 2009, 351, 2243-2270. doi:10.1002/adsc. 200900426
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 2243-2270
    • Zhang, M.1
  • 11
    • 77949381429 scopus 로고    scopus 로고
    • doi:10.1021/cr900184e
    • Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169. doi:10.1021/cr900184e
    • (2010) Chem. Rev. , vol.110 , pp. 1147-1169
    • Lyons, T.W.1    Sanford, M.S.2
  • 13
    • 79952677383 scopus 로고    scopus 로고
    • doi:10.1021/cr100209d
    • Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170-1214. doi:10.1021/cr100209d
    • (2011) J. Chem. Rev. , vol.111 , pp. 1170-1214
    • Bras, J.1    Muzart, J.2
  • 16
    • 70450203450 scopus 로고    scopus 로고
    • doi:10.1002/chem.200901935
    • Jensen, T.; Fristrup, P. Chem.-Eur. J. 2009, 15, 9632-9636. doi:10.1002/chem.200901935
    • (2009) Chem.-Eur. J. , vol.15 , pp. 9632-9636
    • Jensen, T.1    Fristrup, P.2
  • 18
    • 66149101004 scopus 로고    scopus 로고
    • doi:10.1021/ol900355h
    • Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 1911-1914. doi:10.1021/ol900355h
    • (2009) Org. Lett. , vol.11 , pp. 1911-1914
    • Yip, K.-T.1    Zhu, N.-Y.2    Yang, D.3
  • 19
    • 33846644502 scopus 로고    scopus 로고
    • doi:10.1002/ejoc.200600767
    • Wolfe, J. P. Eur. J. Org. Chem. 2007, 571-582. doi:10.1002/ejoc.200600767
    • (2007) Eur. J. Org. Chem. , pp. 571-582
    • Wolfe, J.P.1
  • 20
    • 41449087573 scopus 로고    scopus 로고
    • Oxidative diamination of alkenes with ureas as nitrogen sources: Mechanistic pathways in the presence of a high oxidation state palladium catalyst
    • DOI 10.1021/ja075041a
    • Muñiz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763-773. doi:10.1021/ja075041a (Pubitemid 351455589)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.2 , pp. 763-773
    • Muniz, K.1    Hovelmann, C.H.2    Streuff, J.3
  • 26
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: London
    • Sundberg, R. J. Indoles; Academic Press: London, 1996.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 27
    • 84867812605 scopus 로고    scopus 로고
    • Product class 13: Indole and its derivatives
    • Thomas, E. J., Ed.; Science of Synthesis, Thieme: Stuttgart, Chapter 10.13.
    • Joule, A. J. Product class 13: Indole and its derivatives. In Fused five-membered hetarenes with one heteroatom; Thomas, E. J., Ed.; Science of Synthesis, Vol. 10; Thieme: Stuttgart, 2000; Chapter 10.13..
    • (2000) Fused Five-membered Hetarenes with One Heteroatom , vol.10
    • Joule, A.J.1
  • 30
    • 77956190481 scopus 로고    scopus 로고
    • doi:10.1016/j.ejmech.2010.07.038
    • Gu, W.; Wang, S. Eur. J. Med. Chem. 2010, 45, 4692-4696. doi:10.1016/j.ejmech.2010.07.038
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 4692-4696
    • Gu, W.1    Wang, S.2
  • 33
    • 80052717027 scopus 로고    scopus 로고
    • doi:10.1039/c1ob05750b
    • Vicente, R. Org. Biomol. Chem. 2011, 9, 6469-6480. doi:10.1039/c1ob05750b
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 6469-6480
    • Vicente, R.1
  • 35
    • 80051801186 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2011.06.040
    • Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195-7210. doi:10.1016/j.tet.2011.06.040
    • (2011) Tetrahedron , vol.67 , pp. 7195-7210
    • Taber, D.F.1    Tirunahari, P.K.2
  • 40
    • 79955898620 scopus 로고    scopus 로고
    • doi:10.1021/cr100403z
    • Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR215-PR283. doi:10.1021/cr100403z
    • (2011) Chem. Rev. , vol.111
    • Cacchi, S.1    Fabrizi, G.2
  • 41
    • 78650177163 scopus 로고    scopus 로고
    • doi:10.1007/128-2009-15
    • Beck, E. M.; Gaunt, M. J. Top. Curr. Chem. 2010, 292, 85-121. doi:10.1007/128-2009-15
    • (2010) Top. Curr. Chem. , vol.292 , pp. 85-121
    • Beck, E.M.1    Gaunt, M.J.2
  • 45
    • 0000954930 scopus 로고
    • doi:10.1016/S0040-4020 01 96888-7
    • Tsuji, J.; Nagashima, H. Tetrahedron 1984, 40, 2699-2702. doi:10.1016/S0040-4020 (01) 96888-7
    • (1984) Tetrahedron , vol.40 , pp. 2699-2702
    • Tsuji, J.1    Nagashima, H.2
  • 46
    • 4243241249 scopus 로고
    • doi:10.1021/cr00038a004
    • Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842. doi:10.1021/cr00038a004
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 50
    • 33644658464 scopus 로고    scopus 로고
    • Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles
    • DOI 10.1021/ja058141u
    • Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. Am. Chem. Soc. 2006, 128, 2528-2529. doi:10.1021/ja058141u (Pubitemid 43327917)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.8 , pp. 2528-2529
    • Beck, E.M.1    Grimster, N.P.2    Hatley, R.3    Gaunt, M.J.4
  • 51
    • 17444430801 scopus 로고    scopus 로고
    • Directed palladation: Fine tuning permits the catalytic 2-alkenylation of indoles
    • DOI 10.1039/b417035k
    • Capito, E.; Brown, J. M.; Ricci, A. Chem. Commun. 2005, 1854-1856. doi:10.1039/b417035k (Pubitemid 40547761)
    • (2005) Chemical Communications , Issue.14 , pp. 1854-1856
    • Capito, E.1    Brown, J.M.2    Ricci, A.3
  • 55
    • 33846396118 scopus 로고    scopus 로고
    • Intermolecular cross-coupling of simple arenes via C-H activation by tuning concentrations of arenes and TFA
    • DOI 10.1021/om060889d
    • Li, R.; Jiang, L.; Lu, W. Organometallics 2006, 25, 5973-5975. doi:10.1021/om060889d (Pubitemid 46132483)
    • (2006) Organometallics , vol.25 , Issue.26 , pp. 5973-5975
    • Li, R.1    Jiang, L.2    Lu, W.3
  • 56
    • 34249936878 scopus 로고    scopus 로고
    • The catalytic cross-coupling of unactivated arenes
    • DOI 10.1126/science.1141956
    • Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172-1175. doi:10.1126/science.1141956 (Pubitemid 46877475)
    • (2007) Science , vol.316 , Issue.5828 , pp. 1172-1175
    • Stuart, D.R.1    Fagnou, K.2
  • 61
    • 0037463415 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4039 03 00116-3
    • Beccalli, E. M.; Broggini, G. Tetrahedron Lett. 2003, 44, 1919-1921. doi:10.1016/S0040-4039 (03) 00116-3
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1919-1921
    • Beccalli, E.M.1    Broggini, G.2
  • 62
    • 0141655068 scopus 로고    scopus 로고
    • Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives
    • DOI 10.1021/jo034636v
    • Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625-7628. doi:10.1021/jo034636v (Pubitemid 37186112)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.20 , pp. 7625-7628
    • Abbiati, G.1    Beccalli, E.M.2    Broggini, G.3    Zoni, C.4
  • 63
    • 12344287177 scopus 로고    scopus 로고
    • Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: Regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines
    • DOI 10.1016/j.tet.2004.11.066, PII S0040402004019829
    • Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. Tetrahedron 2005, 61, 1077-1082. doi:10.1016/j.tet.2004.11.066 (Pubitemid 40126713)
    • (2005) Tetrahedron , vol.61 , Issue.5 , pp. 1077-1082
    • Beccalli, E.M.1    Broggini, G.2    Martinelli, M.3    Paladino, G.4
  • 64
    • 42949122684 scopus 로고    scopus 로고
    • Intramolecular palladium-catalyzed oxidative coupling on thiophene and furan rings: Determinant role of the electronic availability of the heterocycle
    • DOI 10.1055/s-2008-1072583
    • Beccalli, E. M.; Borsini, E.; Broggini, G.; Rigamonti, M.; Sottocornola, S. Synlett 2008, 1053-1057. doi:10.1055/s-2008-1072583 (Pubitemid 351613092)
    • (2008) Synlett , Issue.7 , pp. 1053-1057
    • Beccalli, E.M.1    Borsini, E.2    Broggini, G.3    Rigamonti, M.4    Sottocornola, S.5
  • 65
    • 0041624424 scopus 로고    scopus 로고
    • Catalytic C-H bond functionalization with palladium(II): Aerobic oxidative annulations of indoles
    • DOI 10.1021/ja035054y
    • Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579. doi:10.1021/ja035054y (Pubitemid 36975907)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.32 , pp. 9578-9579
    • Ferreira, E.M.1    Stoltz, B.M.2
  • 67
    • 10044267678 scopus 로고    scopus 로고
    • Direct oxidative heck cyclizations: Intramolecular Fujiwara-Moritani arylations for the synthesis of functionalized benzofurans and dihydrobenzofurans
    • DOI 10.1002/anie.200461294
    • Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 6144-6148. doi:10.1002/anie.200461294 (Pubitemid 39611881)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.45 , pp. 6144-6148
    • Zhang, H.1    Ferreira, E.M.2    Stoltz, B.M.3
  • 72
    • 33746618389 scopus 로고    scopus 로고
    • Practical and efficient palladium-promoted synthesis of indole systems containing medium- and large-ring-fused heterocycles
    • DOI 10.1055/s-2006-942398
    • Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G.; Rossi, E. Synthesis 2006, 2404-2412. doi:10.1055/s-2006-942398 (Pubitemid 44146993)
    • (2006) Synthesis , Issue.14 , pp. 2404-2412
    • Beccalli, E.M.1    Broggini, G.2    Martinelli, M.3    Paladino, G.4    Rossi, E.5
  • 73
    • 0037055075 scopus 로고    scopus 로고
    • A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indoledihydroindoloazocine cyclization
    • DOI 10.1021/ja026663t
    • Baran, P. S.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 7904-7905. doi:10.1021/ja026663t (Pubitemid 34755502)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.27 , pp. 7904-7905
    • Baran, P.S.1    Corey, E.J.2
  • 75
    • 4544324311 scopus 로고    scopus 로고
    • New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: Controlling the regioselectivity
    • DOI 10.1021/ol048663z
    • Bandini, M.; Melloni, A.; Umani-Ronchi, A. Org. Lett. 2004, 6, 3199-3202. doi:10.1021/ol048663z (Pubitemid 39233154)
    • (2004) Organic Letters , vol.6 , Issue.18 , pp. 3199-3202
    • Bandini, M.1    Melloni, A.2    Umani-Ronchi, A.3
  • 77
    • 33645927023 scopus 로고    scopus 로고
    • Highly efficient construction of benzene ring in carbazoles by palladium-catalyzed endo-mode oxidative cyclization of 3-(3 -alkenyl) indoles
    • DOI 10.1021/ol060039u
    • Kong, A.; Han, X.; Lu, X. Org. Lett. 2006, 8, 1339-1342. doi:10.1021/ol060039u (Pubitemid 43587433)
    • (2006) Organic Letters , vol.8 , Issue.7 , pp. 1339-1342
    • Kong, A.1    Han, X.2    Lu, X.3
  • 79
    • 30544440070 scopus 로고    scopus 로고
    • Pd-catalyzed cyclization of 1-allyl-2-indolecarboxamides by intramolecular amidation of unactivated ethylenic bond
    • DOI 10.1055/s-2005-922788, D30505ST
    • Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. Synlett 2006, 73-76. doi:10.1055/s-2005-922788 (Pubitemid 43082392)
    • (2006) Synlett , Issue.1 , pp. 73-76
    • Abbiati, G.1    Beccalli, E.2    Broggini, G.3    Martinelli, M.4    Paladino, G.5
  • 81
    • 4143152853 scopus 로고    scopus 로고
    • Palladium-catalyzed cyclization/carboalkoxylation of alkenyl indoles
    • DOI 10.1021/ja046810i
    • Liu, C.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 10250-10251. doi:10.1021/ja046810i (Pubitemid 39100770)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.33 , pp. 10250-10251
    • Liu, C.1    Widenhoefer, R.A.2
  • 82
    • 33644760299 scopus 로고    scopus 로고
    • II-catalyzed arylation/ carboalkoxylation of unactivated olefins with indoles
    • DOI 10.1002/chem.200500787
    • Liu, C.; Widenhoefer, R. A. Chem.-Eur. J. 2006, 12, 2371-2382. doi:10.1002/chem.200500787 (Pubitemid 43344552)
    • (2006) Chemistry - A European Journal , vol.12 , Issue.8 , pp. 2371-2382
    • Liu, C.1    Widenhoefer, R.A.2
  • 85
    • 85064467362 scopus 로고
    • doi:10.1055/s-1993-22593
    • Ji, J.; Lu, X. Synlett 1993, 745-747. doi:10.1055/s-1993-22593
    • (1993) Synlett , pp. 745-747
    • Ji, J.1    Lu, X.2
  • 86
    • 66149175447 scopus 로고    scopus 로고
    • doi:10.1021/ol9007348
    • Han, X.; Lu, X. Org. Lett. 2009, 11, 2381-2384. doi:10.1021/ol9007348
    • (2009) Org. Lett. , vol.11 , pp. 2381-2384
    • Han, X.1    Lu, X.2


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