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Volumn 9, Issue 24, 2007, Pages 4943-4945

Cu(I)-catalyzed intermodular diamination of activated terminal olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; COPPER; CUPROUS CHLORIDE; DIAMINE; UNCLASSIFIED DRUG;

EID: 36849045727     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702061s     Document Type: Article
Times cited : (93)

References (39)
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  • 12
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    • For metal-catalyzed diamination with TsNCh or TsNClNa, see: a
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  • 20
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    • For a related diamination of terminal olefins at allylic and homoallylic carbons via C-H activation, see: Du, H, Yuan, W, Zhao, B, Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496
    • For a related diamination of terminal olefins at allylic and homoallylic carbons via C-H activation, see: Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496.
  • 23
    • 0003593740 scopus 로고
    • For a leading review on diaziridinones, see:, Hassner, A, Ed, John Wiley & Sons, Inc, New York
    • For a leading review on diaziridinones, see: Heine, H. W. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; John Wiley & Sons, Inc.: New York, 1983; p 547.
    • (1983) The Chemistry of Heterocyclic Compounds , pp. 547
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    • Prepared based on reported procedure: Timberlake, J. W.; Alender, J.; Garner, A. W.; Hodges, M. L.; Ozmeral, C.; Szilagyi, S.; Jacobus, J. O. J. Org. Chem. 1981, 46, 2082.
    • Prepared based on reported procedure: Timberlake, J. W.; Alender, J.; Garner, A. W.; Hodges, M. L.; Ozmeral, C.; Szilagyi, S.; Jacobus, J. O. J. Org. Chem. 1981, 46, 2082.
  • 25
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    • 3 (0.1 mL) and tri-n-butylphosphine (0.020 mL, 0.08 mmol). After the mixture was stirred at room temperature for 10 min, styrene (5a) (0.042 g, 0.40 mmol) and di-tert-butylthiadiaziridine 1,1-dioxide (6) (0.124 g, 0.60 mmol) were added (for solid olefins, they were added together with CuCl). The reaction mixture was stirred at 50 °C for 24 h and purified by flash chromatography (silica gel, petroleum ether: ethyl acetatexhloroform = 15:1:1.5) to give the diamination product 7a as a white solid (0.080 g, 65%).
    • 3 (0.1 mL) and tri-n-butylphosphine (0.020 mL, 0.08 mmol). After the mixture was stirred at room temperature for 10 min, styrene (5a) (0.042 g, 0.40 mmol) and di-tert-butylthiadiaziridine 1,1-dioxide (6) (0.124 g, 0.60 mmol) were added (for solid olefins, they were added together with CuCl). The reaction mixture was stirred at 50 °C for 24 h and purified by flash chromatography (silica gel, petroleum ether: ethyl acetatexhloroform = 15:1:1.5) to give the diamination product 7a as a white solid (0.080 g, 65%).
  • 26
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    • The deprotection with BaCO3·HCl has also been investigated with additional substrates. For example, both the rert-butyl and sulfonyl groups of compound 7h were cleanly removed in 91% yield. Compound 7k was deprotected in 70% yield with a slightly modified procedure small amount of ethanol was added to improve solubility of 7k and the reaction time was extended to 24 h, However, compounds 7l-n decomposed under this deprotection condition. For a reductive deprotection of sulfamide with LiAlH4, see ref 5a
    • 4, see ref 5a.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.