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Volumn , Issue 33, 2008, Pages 5507-5510

Silver-catalyzed, manganese-mediated allylation and benzylation reactions of aldehydes and ketones

Author keywords

Allylation reaction; Barbier reaction; Manganese; Radical trap; Silver

Indexed keywords


EID: 56049108368     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800898     Document Type: Article
Times cited : (13)

References (42)
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    • Manganese powder (325 mesh, >99%) may be purchased from Sigma-Aldrich for approximately $5/mol. For comparison, magnesium turnings (>99.5%) and indium powder (99.999%) may be purchased for $2 per mol and $560 per mol, respectively.
    • Manganese powder (325 mesh, >99%) may be purchased from Sigma-Aldrich for approximately $5/mol. For comparison, magnesium turnings (>99.5%) and indium powder (99.999%) may be purchased for $2 per mol and $560 per mol, respectively.
  • 13
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    • 0 in situ; a K/C: A. Fürstner, H. Brunner, Tetrahedron Lett. 1996, 37, 7009-7012;
    • 0 in situ; a) K/C: A. Fürstner, H. Brunner, Tetrahedron Lett. 1996, 37, 7009-7012;
  • 16
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    • TMSCl and indium powder: J. Augé, N. Lubin-Germain, A. Thiaw-Woaye, Tetrahedron Lett. 1996, 40, 9245-9247.
    • d) TMSCl and indium powder: J. Augé, N. Lubin-Germain, A. Thiaw-Woaye, Tetrahedron Lett. 1996, 40, 9245-9247.
  • 17
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    • Chlorosilanes are also key reagents in manganese-mediated, chromium- and nickel-catalyzed Nozaki-Hiyama-Kishi (NHK) allylation reactions, wherein chlorosilane is proposed to facilitate turnover of the resultant chromium alkoxide; a) For a discussion of the mechanism of manganese-mediated NHK reaction, see: A. Fürstner, N. Shi, Chem. Rev. 1999, 99, 991-1046;
    • Chlorosilanes are also key reagents in manganese-mediated, chromium- and nickel-catalyzed Nozaki-Hiyama-Kishi (NHK) allylation reactions, wherein chlorosilane is proposed to facilitate turnover of the resultant chromium alkoxide; a) For a discussion of the mechanism of manganese-mediated NHK reaction, see: A. Fürstner, N. Shi, Chem. Rev. 1999, 99, 991-1046;
  • 22
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    • Copper salts catalyze the manganese-mediated reaction of allyl chloride with aromatic aldehydes: C. J. Li, Y. Meng, X. H. Yi, J. Ma, T. H. Chan, J. Org. Chem. 1998, 63, 7498-7504.
    • Copper salts catalyze the manganese-mediated reaction of allyl chloride with aromatic aldehydes: C. J. Li, Y. Meng, X. H. Yi, J. Ma, T. H. Chan, J. Org. Chem. 1998, 63, 7498-7504.
  • 25
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    • Higher-order organomanganates have been proposed as intermediates in manganese-catalyzed reactions of Grignard reagents with electrophiles; see ref.[3b
    • [3b].
  • 26
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    • One possible mechanism for catalysis would be activation of the halide toward single electron transfer from Mn0. For activation of allylic bromides by indium salts, see: a G. R. Cook, R. Hayashi, Org. Lett. 2006, 8, 1045-1048;
    • 0. For activation of allylic bromides by indium salts, see: a) G. R. Cook, R. Hayashi, Org. Lett. 2006, 8, 1045-1048;
  • 28
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    • An alternative possible mechanism for catalysis would be formation of a nucleophilic allylsilver complex. Silver-catalyzed Sakurai-Hosomi allylation: M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 14556-14557
    • An alternative possible mechanism for catalysis would be formation of a nucleophilic allylsilver complex. Silver-catalyzed Sakurai-Hosomi allylation: M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 14556-14557.
  • 29
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    • A moderate yield of benzylated alcohols can be obtained in a silver-catalyzed, zinc-mediated Barbier reaction: L. W. Bieber, E. C. Storch, I. Malvestiti, M. F. da Silva, Tetrahedron Lett. 1998, 39, 9393-9396;
    • a) A moderate yield of benzylated alcohols can be obtained in a silver-catalyzed, zinc-mediated Barbier reaction: L. W. Bieber, E. C. Storch, I. Malvestiti, M. F. da Silva, Tetrahedron Lett. 1998, 39, 9393-9396;
  • 30
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    • Barbier-type reactions mediated by stoichiometric silver iodide and indium: Z.-L. Shen, Y.-L. Yeo, T. P. Loh, J. Org. Chem. 2008, 73, 3922-3924.
    • b) Barbier-type reactions mediated by stoichiometric silver iodide and indium: Z.-L. Shen, Y.-L. Yeo, T. P. Loh, J. Org. Chem. 2008, 73, 3922-3924.
  • 31
    • 0001618250 scopus 로고    scopus 로고
    • IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; see: A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405-3409.
    • IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; see: A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405-3409.
  • 32
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    • Addition of phosphane ligands such as DIFLUORPHOS and MeDuPhos also resulted in lower yields of homoallylic alcohol
    • Addition of phosphane ligands such as DIFLUORPHOS and MeDuPhos also resulted in lower yields of homoallylic alcohol.
  • 33
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    • Copper-catalyzed, manganese-mediated Wurtz coupling in aqueous media: J. H. Ma, T. H. Chan, Tetrahedron Lett. 1998, 39, 2499-2502;
    • a) Copper-catalyzed, manganese-mediated Wurtz coupling in aqueous media: J. H. Ma, T. H. Chan, Tetrahedron Lett. 1998, 39, 2499-2502;
  • 34
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    • 10-mediated Wurtz coupling: B. C. Gilbert, C. I. Lindsay, P. T. McGrail, A. F. Parsons, D. T. E. Whittaker, Synth. Commun. 1999, 29, 2711-2718;
    • 10-mediated Wurtz coupling: B. C. Gilbert, C. I. Lindsay, P. T. McGrail, A. F. Parsons, D. T. E. Whittaker, Synth. Commun. 1999, 29, 2711-2718;
  • 35
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    • Titaniumand zirconium-catalyzed, manganese-mediated Wurtz coupling: A. F. Barrero, M. M. Herrador, J. F. Q. del Moral, P. Arteaga, J. F. Arteaga, H. R. Dieguez, E. M. Sanchez, J. Org. Chem. 2007, 72, 2988-2995.
    • c) Titaniumand zirconium-catalyzed, manganese-mediated Wurtz coupling: A. F. Barrero, M. M. Herrador, J. F. Q. del Moral, P. Arteaga, J. F. Arteaga, H. R. Dieguez, E. M. Sanchez, J. Org. Chem. 2007, 72, 2988-2995.
  • 36
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    • Certain substrates do not react under our standard allylation conditions. For example, 4-acetamidobenzaldehyde, 4-nitrobenzaldehyde, and 3-hydroxybenzaldehyde afford less than 10% conversion to the requisite homoallylic alcohols.
    • Certain substrates do not react under our standard allylation conditions. For example, 4-acetamidobenzaldehyde, 4-nitrobenzaldehyde, and 3-hydroxybenzaldehyde afford less than 10% conversion to the requisite homoallylic alcohols.
  • 37
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    • Chromium-catalyzed, manganese-mediated pinacol coupling: N. Takenaka, G. Xia, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 13198-13199.
    • Chromium-catalyzed, manganese-mediated pinacol coupling: N. Takenaka, G. Xia, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 13198-13199.
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    • Rieke manganese has been used to prepare benzylic manganese halides: S. H. Kim, R. D. Rieke, J. Org. Chem. 2000, 65, 2322-2330.
    • Rieke manganese has been used to prepare benzylic manganese halides: S. H. Kim, R. D. Rieke, J. Org. Chem. 2000, 65, 2322-2330.
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    • [15b].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.