메뉴 건너뛰기




Volumn 15, Issue 4, 2009, Pages 820-833

Intermolecular olefin functionalisation involving aryl radicals generated from arenediazonium salts

Author keywords

Arenediazonium salts; Aryl radicals; Meerwein arylation; Multicomponent reactions; Olefins; Radical reactions

Indexed keywords

AROMATIC COMPOUNDS; ATOMIC PHYSICS; ATOMIC SPECTROSCOPY; FUNCTIONAL GROUPS; OLEFINS; REACTION KINETICS; SUBSTRATES;

EID: 58449107975     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801306     Document Type: Article
Times cited : (249)

References (196)
  • 1
    • 0000707331 scopus 로고
    • For the rate constants for halogen abstraction from aryl halides by tributyltin radicals, see
    • For the rate constants for halogen abstraction from aryl halides by tributyltin radicals, see: D. P. Curran, C. P. Jasperse, M. J. Totleben, J. Org. Chem. 1991, 56, 7169-7172.
    • (1991) J. Org. Chem , vol.56 , pp. 7169-7172
    • Curran, D.P.1    Jasperse, C.P.2    Totleben, M.J.3
  • 2
    • 35048827803 scopus 로고    scopus 로고
    • For a recent application of aryl radicals (generated by tin-based reagents) in natural product synthesis, see
    • For a recent application of aryl radicals (generated by tin-based reagents) in natural product synthesis, see: F. Li, L. Castle, Org. Lett. 2007, 9, 4033-4036.
    • (2007) Org. Lett , vol.9 , pp. 4033-4036
    • Li, F.1    Castle, L.2
  • 3
    • 46049109074 scopus 로고    scopus 로고
    • For reviews on silicon hydrides in radical chemistry, see
    • For reviews on silicon hydrides in radical chemistry, see: C. Chatgilialoglu, Chem. Eur. J. 2008, 14, 2310-2320;
    • (2008) Chem. Eur. J , vol.14 , pp. 2310-2320
    • Chatgilialoglu, C.1
  • 5
    • 33750350313 scopus 로고    scopus 로고
    • For a recent applications of aryl radicals generated by silicon-based reagents, see: a
    • For a recent applications of aryl radicals generated by silicon-based reagents, see: a) D. P. Curran, A. I. Keller, J. Am. Chem. Soc. 2006, 128, 13706-13707;
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 13706-13707
    • Curran, D.P.1    Keller, A.I.2
  • 7
    • 0001745040 scopus 로고    scopus 로고
    • For replacement of organotin compounds by other reagents, see
    • For replacement of organotin compounds by other reagents, see: P.A. Baguley, J. C. Walton, Angew. Chem. 1998, 110, 3272-3283;
    • (1998) Angew. Chem , vol.110 , pp. 3272-3283
    • Baguley, P.A.1    Walton, J.C.2
  • 8
    • 0032484067 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 3072-3082.
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 3072-3082
  • 9
    • 0000392657 scopus 로고
    • For samarium diiodide mediated formation of aryl radicals, see: a
    • For samarium diiodide mediated formation of aryl radicals, see: a) G. A. Molander, L. S. Haring, J. Org. Chem. 1990, 55, 6171-6176;
    • (1990) J. Org. Chem , vol.55 , pp. 6171-6176
    • Molander, G.A.1    Haring, L.S.2
  • 13
    • 0027209128 scopus 로고
    • For electrochemical generation of aryl radicals, see: a
    • For electrochemical generation of aryl radicals, see: a) C. Combellas, H. Marzouk, C. seeba, A. Thiebault, Synthesis 1993, 788-790;
    • (1993) Synthesis , pp. 788-790
    • Combellas, C.1    Marzouk, H.2    seeba, C.3    Thiebault, A.4
  • 17
    • 24744468986 scopus 로고    scopus 로고
    • For photochemical generations of aryl radicals from, aryl halides, see: a
    • For photochemical generations of aryl radicals from, aryl halides, see: a) Q. Liu, B. Han, W. Zhang, L. Yang, Z.-L. Liu, W. Yu, Synlett 2005, 2248-2250;
    • (2005) Synlett , pp. 2248-2250
    • Liu, Q.1    Han, B.2    Zhang, W.3    Yang, L.4    Liu, Z.-L.5    Yu, W.6
  • 20
    • 2942545129 scopus 로고
    • C. Galli, Chem. Rev. 1988, 88, 765-792.
    • (1988) Chem. Rev , vol.88 , pp. 765-792
    • Galli, C.1
  • 26
    • 33749375419 scopus 로고    scopus 로고
    • For a recent comparison of arenediazonium salts and aryl triazenes, see
    • For a recent comparison of arenediazonium salts and aryl triazenes, see: V. V. Smalius, V. M. Naidan, Russ. J. Gen. Chem. 2006, 76, 1295-1298.
    • (2006) Russ. J. Gen. Chem , vol.76 , pp. 1295-1298
    • Smalius, V.V.1    Naidan, V.M.2
  • 29
    • 0035805276 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1704-1705.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 1704-1705
  • 32
    • 58449113967 scopus 로고    scopus 로고
    • Some reactions rely on the H abstraction by aryl radicals from activated positions-for aryl radicals in protecting and radical-translocating groups, see: L. Feray, N. Kuznetsov, P. Renaud, Radicals in Organic Synthesis, 2 Eds: P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001, pp. 263-270
    • Some reactions rely on the H abstraction by aryl radicals from activated positions-for aryl radicals in protecting and radical-translocating groups, see: L. Feray, N. Kuznetsov, P. Renaud, Radicals in Organic Synthesis, Vol. 2 (Eds: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, pp. 263-270.
  • 33
  • 34
    • 0001728539 scopus 로고
    • Angew Chem. Int. Ed. 1983, 22, 753-764.
    • (1983) Angew Chem. Int. Ed , vol.22 , pp. 753-764
  • 36
    • 0035901673 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1340-1371.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 1340-1371
  • 40
    • 0002523168 scopus 로고    scopus 로고
    • For a review on radical additions to aromatic substrates, see:, Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • For a review on radical additions to aromatic substrates, see: A. Studer, Radicals in Organic Synthesis, Vol. 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, pp. 62-76.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 62-76
    • Studer, A.1
  • 41
    • 33751142878 scopus 로고
    • For a review on Sandmeyer reactions, see: a
    • For a review on Sandmeyer reactions, see: a) F. Minisci, F. Fontana, E. Vismara, Gazz. Chim. Ital. 1993, 123, 9-18;
    • (1993) Gazz. Chim. Ital , vol.123 , pp. 9-18
    • Minisci, F.1    Fontana, F.2    Vismara, E.3
  • 45
    • 0000600785 scopus 로고
    • For a review on the Meerwein arylation, see
    • For a review on the Meerwein arylation, see: C. S. Rondestvedt, Org. React. 1976, 24, 225-259.
    • (1976) Org. React , vol.24 , pp. 225-259
    • Rondestvedt, C.S.1
  • 51
    • 0038800178 scopus 로고    scopus 로고
    • Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • J. A. Murphy, Radicals in Organic Synthesis, Vol. 1 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, pp. 298-314.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 298-314
    • Murphy, J.A.1
  • 54
    • 0031571496 scopus 로고    scopus 로고
    • The low enantioselectivity obtained with optically active copper catalysts in the Meerwein arylation of activated olefins suggests that the carbon-halogen bond is formed by the atom-transfer pathway: H. Brunner, C. Blüchel, M. P. Doyle, J. Organomet. Chem. 1997, 541, 89-95
    • The low enantioselectivity obtained with optically active copper catalysts in the Meerwein arylation of activated olefins suggests that the carbon-halogen bond is formed by the atom-transfer pathway: H. Brunner, C. Blüchel, M. P. Doyle, J. Organomet. Chem. 1997, 541, 89-95.
  • 69
    • 0037009015 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3230-3233;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 3230-3233
  • 71
    • 7244247118 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 5372-5374;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5372-5374
  • 73
    • 37049100296 scopus 로고    scopus 로고
    • T. Okamoto, S. Oka, J. Chem. Soc. Chem. Commun. 1984, 289-291;
    • a) T. Okamoto, S. Oka, J. Chem. Soc. Chem. Commun. 1984, 289-291;
  • 101
    • 0000722245 scopus 로고
    • For the first reports on the radical addition to azides, see: a
    • For the first reports on the radical addition to azides, see: a) S. Kim, G. H. Joe, J. Y. Do, J. Am. Chem. Soc. 1994, 116, 5521-5522;
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 5521-5522
    • Kim, S.1    Joe, G.H.2    Do, J.Y.3
  • 104
    • 0005324975 scopus 로고
    • For a first report on aryl diazonium salts as nitrogen-centred radical scavenegers, see
    • For a first report on aryl diazonium salts as nitrogen-centred radical scavenegers, see: I. Al Adel, B. A. Salami, J. Levisalles, H. Rudler, Bull Soc. Chim. Fr. 1976, 934-938.
    • (1976) Bull Soc. Chim. Fr , pp. 934-938
    • Al Adel, I.1    Salami, B.A.2    Levisalles, J.3    Rudler, H.4
  • 113
    • 58449095465 scopus 로고    scopus 로고
    • see also reference [23].
    • c) see also reference [23].
  • 121
    • 58449126165 scopus 로고    scopus 로고
    • Iron-catalysed aqueous hydrolysis of analoguous azo compounds 24 to give aldehydes 25 is not expected to occur to a major extent. The para-cyano-substituted analogue of compound 24 should even be more stable towards hydrolysis than its pora-chloro derivative.
    • Iron-catalysed aqueous hydrolysis of analoguous azo compounds 24 to give aldehydes 25 is not expected to occur to a major extent. The para-cyano-substituted analogue of compound 24 should even be more stable towards hydrolysis than its pora-chloro derivative.
  • 123
    • 0032528238 scopus 로고    scopus 로고
    • For recent reports on nonradical carbohydroxylation, see: a
    • For recent reports on nonradical carbohydroxylation, see: a) H. Nakamura, M. Sekido, M. Ito, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 6838-6839;
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 6838-6839
    • Nakamura, H.1    Sekido, M.2    Ito, M.3    Yamamoto, Y.4
  • 127
    • 0742304172 scopus 로고    scopus 로고
    • S. P. Miller, J. B. Morgan, F. J. Nepveux V, J. P. Marken, Org. Lett. 2004, 6, 131-133;
    • e) S. P. Miller, J. B. Morgan, F. J. Nepveux V, J. P. Marken, Org. Lett. 2004, 6, 131-133;
  • 129
    • 0000745524 scopus 로고
    • For kinetics of nitroxide radical trapping solvent effects, see
    • For kinetics of nitroxide radical trapping (solvent effects), see: A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 4983-4992.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 4983-4992
    • Beckwith, A.L.J.1    Bowry, V.W.2    Ingold, K.U.3
  • 130
    • 33344460519 scopus 로고    scopus 로고
    • For the photochemical formation of aryl radicals in the presence of TEMPO, see
    • For the photochemical formation of aryl radicals in the presence of TEMPO, see: M. R. Heinrich, M. Kirschstein, Tetrahedron Lett. 2006, 47, 2115-2118.
    • (2006) Tetrahedron Lett , vol.47 , pp. 2115-2118
    • Heinrich, M.R.1    Kirschstein, M.2
  • 131
    • 58449086503 scopus 로고    scopus 로고
    • 1157-11.60;
    • a) A. Studer, Angew. Chem. 2000, 112, 1157-11.60;
    • (2000) Angew. Chem , vol.112
    • Studer, A.1
  • 132
    • 0034678011 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 1108-1111;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 1108-1111
  • 137
    • 0035781101 scopus 로고    scopus 로고
    • For the persistant radical effect (PRE), see: a) H. Fischer, Chem. Rev. 2001, 101, 3581-3610;
    • For the persistant radical effect (PRE), see: a) H. Fischer, Chem. Rev. 2001, 101, 3581-3610;
  • 138
  • 142
    • 0042467431 scopus 로고    scopus 로고
    • For the Kharash-Sosnovsky allylic C-H oxidation, see:, Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • For the Kharash-Sosnovsky allylic C-H oxidation, see: T. Katsuki, Radicals in Organic Synthesis, Vol.2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, pp. 113-126.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 113-126
    • Katsuki, T.1
  • 144
    • 0000652394 scopus 로고    scopus 로고
    • For reviews on xanthates in radical, chemistry, see: a
    • For reviews on xanthates in radical, chemistry, see: a) S. Z. Zard, Angew. Chem. 1997, 109, 724-737;
    • (1997) Angew. Chem , vol.109 , pp. 724-737
    • Zard, S.Z.1
  • 163
    • 0010779588 scopus 로고
    • For alternative reaction mechanisms, see: a
    • For alternative reaction mechanisms, see: a) O. Vogl, C. S. Rondestvedt, J. Am. Chem. Soc. 1955, 77, 3067-3069;
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 3067-3069
    • Vogl, O.1    Rondestvedt, C.S.2
  • 167
    • 58449111387 scopus 로고    scopus 로고
    • see also reference [30].
    • e) see also reference [30].
  • 171
    • 58449102833 scopus 로고    scopus 로고
    • [44]
    • [44]
  • 174
    • 33749375419 scopus 로고    scopus 로고
    • For a recent Meerwein reaction of sulfonyl-1,3-butadienes leading to the 1,2-adducts, see: V. V. Smalius, V. M. Naidan, Russ. J. Gen. Chem. 2006, 76, 1295-1298.
    • For a recent Meerwein reaction of sulfonyl-1,3-butadienes leading to the 1,2-adducts, see: V. V. Smalius, V. M. Naidan, Russ. J. Gen. Chem. 2006, 76, 1295-1298.
  • 176
    • 0036262227 scopus 로고    scopus 로고
    • For modified versions of the Meerwein reaction with respect to the counterion of the diazonium salt, see: N. D. Obushak, M. B. Lyakhovich, E. E. Bilaya, Russ J. Org. Chem. 2002, 38, 38-46
    • For modified versions of the Meerwein reaction with respect to the counterion of the diazonium salt, see: N. D. Obushak, M. B. Lyakhovich, E. E. Bilaya, Russ J. Org. Chem. 2002, 38, 38-46.
  • 177
    • 58449118412 scopus 로고    scopus 로고
    • Meerwein arylation of non-activated olefins other than 2-methallylchloride, see; N. D. Obushak, V. V. Karpyak, N. I. Ganushchak, E. P. Kovalchuk, V. P. Tikhonov, Russ. J. Org. Chem. 1993, 29, 1149-1155.
    • Meerwein arylation of non-activated olefins other than 2-methallylchloride, see; N. D. Obushak, V. V. Karpyak, N. I. Ganushchak, E. P. Kovalchuk, V. P. Tikhonov, Russ. J. Org. Chem. 1993, 29, 1149-1155.
  • 189
    • 37049092779 scopus 로고
    • For possible iodine-centred radical, scavengers, see: a
    • For possible iodine-centred radical, scavengers, see: a) C. Galli, J. Chem. Soc. Perkin Trans. 2 1981, 1459-1461;
    • (1981) J. Chem. Soc. Perkin Trans. 2 , pp. 1459-1461
    • Galli, C.1
  • 194
    • 58449111998 scopus 로고    scopus 로고
    • -, which could act as suitable scavenger, has been reported in iodide-induced dediazoniation reaction; see reference [93b].
    • -, which could act as suitable scavenger, has been reported in iodide-induced dediazoniation reaction; see reference [93b].
  • 195
    • 0032328177 scopus 로고    scopus 로고
    • For iodoarylation of activated olefins and application to the synthesis of heterocycles, see
    • For iodoarylation of activated olefins and application to the synthesis of heterocycles, see: N. D. Obushak, V. S. Matiichuk, N. I. Ganushchak, Russ. J. Org. Chem. 1998, 34, 239-244.
    • (1998) Russ. J. Org. Chem , vol.34 , pp. 239-244
    • Obushak, N.D.1    Matiichuk, V.S.2    Ganushchak, N.I.3
  • 196
    • 58449096836 scopus 로고
    • For the iodoarylation of 1,3-butadienes in the absence of copper, see
    • For the iodoarylation of 1,3-butadienes in the absence of copper, see: N. I. Ganushchak, N. D. Obushak, O. P. Polishchuk, Zh. Org. Khim. 1984, 20, 595-596.
    • (1984) Zh. Org. Khim , vol.20 , pp. 595-596
    • Ganushchak, N.I.1    Obushak, N.D.2    Polishchuk, O.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.