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Volumn 44, Issue 8, 2003, Pages 1541-1544

Base-free oxidative homocoupling of arylboronic esters

Author keywords

Biaryls; Boron; Homocoupling; Oxygen; Palladium

Indexed keywords

1,3 BIS(DIPHENYLPHOSPHINO)PROPANE; ESTER DERIVATIVE; FUNCTIONAL GROUP; OXYGEN; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037450443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00023-6     Document Type: Article
Times cited : (126)

References (46)
  • 2
    • 0001786881 scopus 로고    scopus 로고
    • Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim
    • (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp. 49-97.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 49-97
    • Suzuki, A.1
  • 21
    • 5244346814 scopus 로고    scopus 로고
    • Recently, transition metal-catalyzed addition of organoboron compounds to unsaturated organic compounds without added base has attracted considerable attention, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229;
    • (1997) Organometallics , vol.16 , pp. 4229
    • Sakai, M.1    Hayashi, H.2    Miyaura, N.3
  • 28
    • 0742313889 scopus 로고    scopus 로고
    • There has been only one report on the palladium-catalyzed base-free oxidative homocoupling of organoboronic acids, however, the low to moderate product yields and the formation of undesirable side-products seem to impair its synthetic utility, see: Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
    • (1996) J. Org. Chem. , vol.61 , pp. 2346
    • Moreno-Mañas, M.1    Pérez, M.2    Pleixats, R.3
  • 29
    • 0001403744 scopus 로고
    • Although the reaction of organoboranes with oxygen was reported to give the corresponding alcohols, no trace of p-cresol (4) was detected in the reaction of 3 without using the catalyst. This result would rule out the direct oxidation pathway with oxygen in the formation of 4. For the oxidation of trialkylboranes with oxygen, see: Brown, H. C.; Midland, M. M.; Kabalka, G. W. J. Am. Chem. Soc. 1971, 93, 1024.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 1024
    • Brown, H.C.1    Midland, M.M.2    Kabalka, G.W.3
  • 35
    • 0013032936 scopus 로고
    • Although the ultimate fate of 10 was not identified at present, boron peroxide should decompose into boronic acid, its esters, etc. For thermal decomposition of organoboron peroxides, see: Maslennikov, V. P.; Makin, G. I.; Alyasov, V. N.; Aleksandrov, Y. A. Zh. Obshch. Khim. 1973, 43, 1972.
    • (1973) Zh. Obshch. Khim. , vol.43 , pp. 1972
    • Maslennikov, V.P.1    Makin, G.I.2    Alyasov, V.N.3    Aleksandrov, Y.A.4
  • 36
    • 0003441482 scopus 로고
    • Wiley: Chichester; Chap. 3
    • In general, in situ reoxidation of a palladium(0) complex to a palladium(II) complex with molecular oxygen alone is not an easy process, however, DMSO has been reported to be an exceptionally efficient solvent for this purpose: (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; Chap. 3;
    • (1995) Palladium Reagents and Catalysts
    • Tsuji, J.1
  • 44
    • 0012985333 scopus 로고    scopus 로고
    • note
    • Since addition of 10 mol% of galvinoxyl (a radical scavenger) to the homocoupling of 1b did not affect both the reaction rate and the yield of 2b, we can eliminate the possibility that the present homocoupling proceeds through oxygen-mediated radical pathways. For the radical-chain process observed in the reaction of trialkylboranes with oxygen, see Ref. 6.
  • 45
    • 0000975959 scopus 로고    scopus 로고
    • Liebeskind, L. S., Ed.; JAI Press: London
    • Palladium-catalyzed homocoupling of organoboron compounds using a base and oxygen have also been considered to proceed through palladium(II) peroxide, see: (a) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1998; Vol. 6, pp. 187-243;
    • (1998) Advances in Metal-Organic Chemistry , vol.6 , pp. 187-243
    • Miyaura, N.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.