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Volumn 27, Issue 15, 2008, Pages 3996-4004

Palladium-catalyzed oxidative coupling of 2-alkylfurans with olefins through C-H activation: Synthesis of difurylalkanes

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACIDS; ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; COMPLEXATION; COMPUTER NETWORKS; ESTERS; LABELING; OLEFINS; ORGANIC COMPOUNDS; PALLADIUM COMPOUNDS;

EID: 50549091342     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8004433     Document Type: Article
Times cited : (37)

References (82)
  • 28
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    • For a review on the synthesis and the reactivity of furyl(aryl)methanes, see
    • For a review on the synthesis and the reactivity of furyl(aryl)methanes, see: Butin, A. V.; Stroganova, T. A.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1999, 35, 757-787.
    • (1999) Chem. Heterocycl. Compd , vol.35 , pp. 757-787
    • Butin, A.V.1    Stroganova, T.A.2    Kul'nevich, V.G.3
  • 43
    • 33845378909 scopus 로고    scopus 로고
    • 2H, which can act as a source of hydrogen species under palladium catalysis; see: Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129-170. Therefore, the formation of the β,β-diaryl carbonyl compounds could also come from a double Heck reaction followed by a consecutive reduction.
    • 2H, which can act as a source of hydrogen species under palladium catalysis; see: Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129-170. Therefore, the formation of the β,β-diaryl carbonyl compounds could also come from a double Heck reaction followed by a consecutive reduction.
  • 44
    • 0000540618 scopus 로고    scopus 로고
    • The isomerization of alkenes with palladium salts is more efficient in trifluoroacetic acid than in acetic acid: Cramer, R, Lindsey, R. V. J. Am. Chem. Soc. 1966, 88, 3534-3544
    • The isomerization of alkenes with palladium salts is more efficient in trifluoroacetic acid than in acetic acid: Cramer, R.; Lindsey, R. V. J. Am. Chem. Soc. 1966, 88, 3534-3544.
  • 50
  • 51
    • 0001560713 scopus 로고
    • For a Wacker reaction with isosafrole, see
    • For a Wacker reaction with isosafrole, see: Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088.
    • (1982) Tetrahedron Lett , vol.23 , pp. 3085-3088
    • Tsuji, J.1    Nagashima, H.2    Sato, K.3
  • 53
    • 0037241494 scopus 로고    scopus 로고
    • It has been shown that 2-methylfuran (2) is more nucleophilic than styrene (1f, 1, E)-prop-1-enyl)benzene (1b, and (2-methylallyl)benzene; see: Mayr, H, Kempf, B, Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77
    • It has been shown that 2-methylfuran (2) is more nucleophilic than styrene (1f), 1-((E)-prop-1-enyl)benzene (1b), and (2-methylallyl)benzene; see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
  • 54
    • 50549099639 scopus 로고    scopus 로고
    • 3c
    • 3c
  • 55
    • 0000750426 scopus 로고
    • The efficiency of the Heck reaction of vinyl bromides with alkenes, in the presence of tetraphosphine/Pd catalyst, follow the order n-butyl acrylates > styrene (If) > allylbenzene (la, Acrylates are known to undergo a faster insertion process than styrenes; see: a
    • Acrylates are known to undergo a faster insertion process than styrenes; see: (a) Heck, R. F. J. Am. Chem. Soc. 1971, 93, 6896-6901. The efficiency of the Heck reaction of vinyl bromides with alkenes, in the presence of tetraphosphine/Pd catalyst, follow the order n-butyl acrylates > styrene (If) > allylbenzene (la);
    • (1971) J. Am. Chem. Soc , vol.93 , pp. 6896-6901
    • Heck, R.F.1
  • 57
    • 84926121843 scopus 로고    scopus 로고
    • β-Hydride elimination is one of the major decomposition pathways for metal alkyl complexes: Crabtree, R. H. The Organometallic Chemistry of the Transition Metals; Wiley: New York, 1994.
    • β-Hydride elimination is one of the major decomposition pathways for metal alkyl complexes: Crabtree, R. H. The Organometallic Chemistry of the Transition Metals; Wiley: New York, 1994.
  • 59
    • 50549093250 scopus 로고    scopus 로고
    • Reductive eliminations occur faster with metal hydrides than with metal alkyls.23
    • 23.
  • 60
    • 33750858930 scopus 로고    scopus 로고
    • Recent references: (a) Enquist, P.-A.; Nilsson, P.; Sjöberg, P.; Larhed, M. J. Org. Chem. 2006, 71, 8779-8786.
    • Recent references: (a) Enquist, P.-A.; Nilsson, P.; Sjöberg, P.; Larhed, M. J. Org. Chem. 2006, 71, 8779-8786.
  • 72
    • 50549094044 scopus 로고    scopus 로고
    • These clusters could also be associated with the species El.
    • These clusters could also be associated with the species El.
  • 78
    • 50549102737 scopus 로고    scopus 로고
    • Traces of 3f were sometimes detected in the coupling of 1f with 2, and 3f could interact with palladium catalytic species.
    • Traces of 3f were sometimes detected in the coupling of 1f with 2, and 3f could interact with palladium catalytic species.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.