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Volumn 5, Issue 7, 2003, Pages 979-982

Novel route to azobenzenes via Pd-catalyzed coupling reactions of aryl hydrazides with aryl halides, followed by direct oxidations

Author keywords

[No Author keywords available]

Indexed keywords

AZOBENZENE DERIVATIVE; HALIDE; HYDRAZIDE DERIVATIVE; PALLADIUM;

EID: 0141634145     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027311u     Document Type: Article
Times cited : (90)

References (36)
  • 8
    • 0002568406 scopus 로고
    • Durr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam
    • (h) Ichimura, K. Photochromism: Molecules and Systems; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; p 903.
    • (1990) Photochromism: Molecules and Systems , pp. 903
    • Ichimura, K.1
  • 12
    • 0003759015 scopus 로고
    • VCH: New York
    • For review of azo dyes, see: (a) Zollinger, H. Diazo Chemistry I. Aromatic and Heteroaromatic Compounds; VCH: New York, 1994. (b) Hegarty, A. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: New York, 1978; Part 2, pp 545-551. (c) The Chemistry of Synthetic Dyes; Venkataraman, K., Ed.; Academic Press: New York, 1970; Vols. 1-7.
    • (1994) Diazo Chemistry I. Aromatic and Heteroaromatic Compounds
    • Zollinger, H.1
  • 13
    • 0000364631 scopus 로고
    • Patai, S., Ed.; Wiley: New York
    • For review of azo dyes, see: (a) Zollinger, H. Diazo Chemistry 1. Aromatic and Heteroaromatic Compounds; VCH: New York, 1994. (b) Hegarty, A. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: New York, 1978; Part 2, pp 545-551. (c) The Chemistry of Synthetic Dyes; Venkataraman, K., Ed.; Academic Press: New York, 1970; Vols. 1-7.
    • (1978) The Chemistry of Diazonium and Diazo Groups , Issue.2 PART , pp. 545-551
    • Hegarty, A.F.1
  • 14
    • 0003968673 scopus 로고
    • Academic Press: New York
    • For review of azo dyes, see: (a) Zollinger, H. Diazo Chemistry 1. Aromatic and Heteroaromatic Compounds; VCH: New York, 1994. (b) Hegarty, A. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: New York, 1978; Part 2, pp 545-551. (c) The Chemistry of Synthetic Dyes; Venkataraman, K., Ed.; Academic Press: New York, 1970; Vols. 1-7.
    • (1970) The Chemistry of Synthetic Dyes , vol.1-7
    • Venkataraman, K.1
  • 28
    • 0141447888 scopus 로고    scopus 로고
    • note
    • 2 when reacted with aryl halides beating substituents at the ortho-position.
  • 30
    • 0141782794 scopus 로고    scopus 로고
    • note
    • 3, and 1.5 mL of anhydrous toluene at room temperature. The resulting solution was stirred for 30 min at room temperature before being heated at 110°C. After 1 h, the reaction mixture was cooled, concentrated in vacuo, and chromatographed (hexanes/EtOAc = 9/1) to afford 41 mg of 3h in 91% yield.
  • 35
    • 0141559480 scopus 로고    scopus 로고
    • note
    • 2 (3 mL) were added pyridine (0.8 mL; 0.094 mmol; 1.2 equiv) and NBS (17 mg; 0.094 mmol; 1.2 equiv) at room temperature. The reaction mixture was stirred for 2 h at room temperature, concentrated in vacuo, and purified by column chromatography (hexanes/EtOAc = 10/1) to afford 18 mg of the azobenzene 5b in 84% yield.
  • 36
    • 0141670881 scopus 로고    scopus 로고
    • note
    • We isolated brominated N-Boc diaryl hydrazine (Br ortho to the OMe group) as a byproduct in 20% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.