메뉴 건너뛰기




Volumn 131, Issue 49, 2009, Pages 17750-17752

N,N-diethyl O-carbamate: Directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID; CHEMICAL EQUATIONS; CROSS-COUPLINGS; CRUCIAL PARAMETERS; DIRECTED ORTHO METALATION; METALATIONS; ROLE OF WATER; STABLE CATALYSTS; SUZUKI-MIYAURA; SUZUKI-MIYAURA CROSS-COUPLING;

EID: 71749088399     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907700e     Document Type: Article
Times cited : (214)

References (69)
  • 3
    • 20544450502 scopus 로고    scopus 로고
    • Diederich, F., Meijere, A., Eds.; Wiley-VCH: Weinheim
    • (c) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Meijere, A., Eds.; Wiley-VCH: Weinheim, 2004; Vol.2.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.2
  • 5
    • 84903810283 scopus 로고    scopus 로고
    • Cepanec, I. Elsevier: Amsterdam, Netherlands.
    • (a) Synthesis of Biaryls; Cepanec, I. Elsevier: Amsterdam, Netherlands. 2004; 17-29.
    • (2004) Synthesis of Biaryls , pp. 17-29
  • 27
    • 67650558689 scopus 로고    scopus 로고
    • For a sequential DoM-Suzuki-Miyaura coupling of an arylboronic acid bearing an attached DMG, see
    • (b) For a sequential DoM-Suzuki-Miyaura coupling of an arylboronic acid bearing an attached DMG, see Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502-7503.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7502-7503
    • Ihara, H.1    Suginome, M.2
  • 30
    • 71749113063 scopus 로고    scopus 로고
    • Synthesis, coupling and reductive cleavage of phenanthrol 9-O-carbamates: Rantanen, T.; Jorgensen, K.; Snieckus, V. in progress
    • Synthesis, coupling and reductive cleavage of phenanthrol 9-O-carbamates: Rantanen, T.; Jorgensen, K.; Snieckus, V. in progress.
  • 31
    • 71749088188 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Waterloo
    • Puumala, K. A., Ph.D. Thesis, University of Waterloo, 1997.
    • (1997)
    • Puumala, K.A.1
  • 36
    • 53849146742 scopus 로고    scopus 로고
    • For application to the synthesis of heterocycles and natural products, see: (a)
    • For application to the synthesis of heterocycles and natural products, see: (a) Macklin, T. K.; Reed, M. A.; Snieckus, V. Angew. Chem., Int. Ed. 2008, 9, 1507-1509.
    • (2008) Angew. Chem., Int. Ed. , vol.9 , pp. 1507-1509
    • Macklin, T.K.1    Reed, M.A.2    Snieckus, V.3
  • 38
    • 33750318730 scopus 로고    scopus 로고
    • For insightful mechanistic studies on the anionic ortho-Fries rearrangement, see
    • (c) For insightful mechanistic studies on the anionic ortho-Fries rearrangement, see Singh, K. J.; Collum, D. B. J. Am. Chem. Soc. 2006, 128, 13753-13760.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 13753-13760
    • Singh, K.J.1    Collum, D.B.2
  • 39
    • 71749120808 scopus 로고    scopus 로고
    • note
    • During the course of our work, we learned of the studies of Garg and coworkers (accompanying Communication) which, in addition to O-carbamate systems, significantly expand the Suzuki-Miyaura reaction to carbonates and O-sulfamates. We are grateful to Prof. Garg for liberal exchange of results and for agreement to consecutive publication.
  • 40
    • 71749111528 scopus 로고    scopus 로고
    • note
    • 2 was observed to undergo rapid oxidation when maintained outside of the glove box, thus giving irreproducible results. This was also noted by Garg and co-workers; see ref 12.
  • 45
    • 71749089841 scopus 로고    scopus 로고
    • For observation of metal contaminants in other catalyzed reactions, see: (a)
    • For observation of metal contaminants in other catalyzed reactions, see: (a) Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 2-4.
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 2-4
    • Buchwald, S.L.1    Bolm, C.2
  • 49
    • 71749087535 scopus 로고    scopus 로고
    • note
    • 1H NMR immediately prior to use (see Supporting Information).
  • 50
    • 71749096204 scopus 로고    scopus 로고
    • For comment on similar observations, see
    • (b) For comment on similar observations, see: Storgaard, M.; Ellman, J. A. Org. Synth. 2009, 86, 360-373.
    • (2009) Org. Synth. , vol.86 , pp. 360-373
    • Storgaard, M.1    Ellman, J.A.2
  • 52
    • 12344284768 scopus 로고    scopus 로고
    • Catalyzed cross-couplings of boroxines
    • (b) Catalyzed cross-couplings of boroxines: Goossen, L. J.; Paetzold, J. Adv. Synth. Catal 2004, 346, 1665-1668.
    • (2004) Adv. Synth. Catal , vol.346 , pp. 1665-1668
    • Goossen, L.J.1    Paetzold, J.2
  • 54
    • 71749094575 scopus 로고    scopus 로고
    • note
    • No or any other product was isolated or detected by GC/MS under these conditions.
  • 56
    • 71749117136 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 58
    • 71749099190 scopus 로고    scopus 로고
    • note
    • 12 (Table 1, entry 7), no product or poor yield of product was obtained.
  • 59
    • 68149110231 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Shi reported this transformation
    • During the preparation of this manuscript, Shi reported this transformation: Yu, D.-G.; Yu, M.; Guan, B.-T.; Li, B.-J.; Zheng, Y.; Wu, Z.-H.; Shi, Z.-J. Org. Lett. 2009, 11, 3374-3377.
    • (2009) Org. Lett. , vol.11 , pp. 3374-3377
    • Yu, D.-G.1    Yu, M.2    Guan, B.-T.3    Li, B.-J.4    Zheng, Y.5    Wu, Z.-H.6    Shi, Z.-J.7
  • 67
    • 71749085487 scopus 로고    scopus 로고
    • note
    • The low yield of 8 is a result of reductive cleavage and arylation of benzofuran rather than low conversion of 7 owing to steric hindrance effects.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.