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Volumn 73, Issue 7, 2008, Pages 2668-2673

Boron trihalide mediated alkyne-aldehyde coupling reactions: A mechanistic investigation

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; LOW TEMPERATURE EFFECTS; REACTION KINETICS; STEREOCHEMISTRY;

EID: 41649111948     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702493j     Document Type: Article
Times cited : (22)

References (75)
  • 50
    • 0001154257 scopus 로고    scopus 로고
    • Grignard-like addition of 9-BBN derivatives to aldehydes and ketones, see: (a) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577.
    • Grignard-like addition of 9-BBN derivatives to aldehydes and ketones, see: (a) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577.
  • 55
    • 41649120636 scopus 로고    scopus 로고
    • The X-ray molecular structure was reported earlier and supported the NMR assignment; see ref 11. A crystal structure of a closely related E,E isomer, 10b, is reported in this summary. See Supporting Information
    • The X-ray molecular structure was reported earlier and supported the NMR assignment; see ref 11. A crystal structure of a closely related E,E isomer, 10b, is reported in this summary. See Supporting Information.
  • 57
    • 0037471219 scopus 로고    scopus 로고
    • For transition-metal-free Suzuki-coupling reaction, see: a
    • For transition-metal-free Suzuki-coupling reaction, see: (a) Leadbeater, N. E.; Marco, M. Angew. Chem., Int. Ed., 2003, 42, 1407.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 1407
    • Leadbeater, N.E.1    Marco, M.2
  • 63
    • 22244490027 scopus 로고    scopus 로고
    • Other evidence supporting a cationic mechanism includes the ring opening of a cyclopropyl group and the racemization of a chiral center in benzyloxide derivatives in the coupling reaction of benzyloxides and vinylboron dihalides. See: Kabalka, G. W, Yao, M.-L, Borella, S, Wu, Z. Org. Lett. 2005, 7, 2865
    • Other evidence supporting a cationic mechanism includes the ring opening of a cyclopropyl group and the racemization of a chiral center in benzyloxide derivatives in the coupling reaction of benzyloxides and vinylboron dihalides. See: Kabalka, G. W.; Yao, M.-L.; Borella, S.; Wu, Z. Org. Lett. 2005, 7, 2865.
  • 64
    • 41649109682 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 65
    • 0000309858 scopus 로고    scopus 로고
    • It is reported that the addition of benzylic carbocation to terminal alkynes stereoselectively gives (Z)-alkenyl halides. See: Marcuzzi, F, Melloni, G, Modena, G. J. Org. Chem. 1979, 44, 3022
    • It is reported that the addition of benzylic carbocation to terminal alkynes stereoselectively gives (Z)-alkenyl halides. See: Marcuzzi, F.; Melloni, G.; Modena, G. J. Org. Chem. 1979, 44, 3022.
  • 66
    • 33749033874 scopus 로고    scopus 로고
    • 3N-mediated conversion of propargyl alcohols to chloroallenes; see: Karunakar, G. V.; Periasamy, M. J. Org. Chem. 2006, 71, 7463.
    • 3N-mediated conversion of propargyl alcohols to chloroallenes; see: Karunakar, G. V.; Periasamy, M. J. Org. Chem. 2006, 71, 7463.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.