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Volumn 52, Issue 4, 2011, Pages 518-522

A base-free, one-pot diazotization/cross-coupling of anilines with arylboronic acids

Author keywords

Aryl amine; Diazotization; Pd catalyzed; Suzuki Miyaura coupling

Indexed keywords

ANILINE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM;

EID: 78650524243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.099     Document Type: Article
Times cited : (37)

References (41)
  • 13
    • 77956903468 scopus 로고    scopus 로고
    • 10.3762/bjoc.6.70
    • For selected recent examples of using arenediazonium salts in Pd-catalyzed cross-coupling reactions, see: G. Nan, F. Ren, and M. Luo Beilstein J. Org. Chem. 6 2010 70 10.3762/bjoc.6.70
    • (2010) Beilstein J. Org. Chem. , vol.6 , pp. 70
    • Nan, G.1    Ren, F.2    Luo, M.3
  • 27
    • 0003905534 scopus 로고
    • B. S Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell, 5th ed. Longman Singapore
    • B. S Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell, Vogel's Textbook of Practical Organic Chemistry 5th ed. 1989 Longman Singapore
    • (1989) Vogel's Textbook of Practical Organic Chemistry
  • 38
    • 78650519777 scopus 로고    scopus 로고
    • note
    • tBuONO (134 mg, 1.3 equiv), and HOAc (60 mg, 1.0 equiv) were then added in succession by syringe. The resulting reaction mixture was allowed to stir at 90 °C for 8 h. The solution was then concentrated under reduced pressure and the crude residue was purified by flash column chromatography with petroleum ether to give 4-methoxy-4′- methylbiphenyl 3b (152 mg, 77%).
  • 39
    • 78650519701 scopus 로고    scopus 로고
    • note
    • tBuONO (108 mg, 1.05 equiv), and HOAc (60 mg, 1.0 equiv) were added in succession by syringe and this reaction mixture was stirred for 5 min. Then the solution containing the newly generated diazonium salt was transferred to the above Schlenk round bottle by syringe. In the course of this transfer, another 2 mL DMF was added to the reaction system. The resulting reaction solution was stirred at 90 °C for 10 h. The solution was then concentrated under reduced pressure and the crude residue was purified by flash column chromatography (petroleum ether/EtOAc = 30:1) to afford the product ethyl biphenyl-4-carboxylate 3o (113 mg, 50%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.