메뉴 건너뛰기




Volumn 15, Issue 3, 2009, Pages 793-797

Selective benzylic and allylic alkylation of protic nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds

Author keywords

Allylic compounds; Benzylic compounds; Carbon nucleophiles; Oxygen heterocycles; Sulfur

Indexed keywords

ACIDS; ALKYLATION; AMIDES; AMINES; CHEMICAL REACTIONS; ESTERS; HYDROCARBONS; KETONES; ORGANIC COMPOUNDS; OXYGEN; SILANES; SUGAR (SUCROSE); SULFUR; SULFUR COMPOUNDS;

EID: 58449134253     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801665     Document Type: Article
Times cited : (92)

References (21)
  • 1
    • 58449083392 scopus 로고    scopus 로고
    • For a review, see: G. A. Olah, R. Krishnamurti, G. K. Surya in Comprehensive Organic Synthesis, (Eds. : B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 3, pp. 293-339.
    • For a review, see: G. A. Olah, R. Krishnamurti, G. K. Surya in Comprehensive Organic Synthesis, (Eds. : B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, Vol. 3, pp. 293-339.
  • 2
    • 58449104540 scopus 로고    scopus 로고
    • Although benzylic and allylic sp3 carbon-nitrogen bonds can be cleaved by certain metals and strong bases, benzylic and allylic amine derivatives have hardly been exploited as useful alkylating agents. For reviews, see: a T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed, Wiley: New York, 1999;
    • 3 carbon-nitrogen bonds can be cleaved by certain metals and strong bases, benzylic and allylic amine derivatives have hardly been exploited as useful alkylating agents. For reviews, see: a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley: New York, 1999;
  • 5
    • 31044438051 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 629-633;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 629-633
  • 9
    • 0037037851 scopus 로고    scopus 로고
    • For studies on the enhanced catalytic activity of metal Lewis acids with silicon Lewis acids in the cleavage of sp3 carbon-halogen and sp 3 carbon-oxygen bonds, see: a Y. Onishi, T. Ito, M. Yasuda, A. Baba, Tetrahedron 2002, 58, 8227-8235;
    • 3 carbon-oxygen bonds, see: a) Y. Onishi, T. Ito, M. Yasuda, A. Baba, Tetrahedron 2002, 58, 8227-8235;
  • 11
    • 40149107277 scopus 로고    scopus 로고
    • We recently found that a few Lewis acids in combination with TMSCl were effective in catalyzing the nucleophilic additions to imines. See: a C.-R. Liu, M.-B. Li, C.-F. Yang, S.-K. Tian, Chem. Commun. 2008, 1249-1251;
    • We recently found that a few Lewis acids in combination with TMSCl were effective in catalyzing the nucleophilic additions to imines. See: a) C.-R. Liu, M.-B. Li, C.-F. Yang, S.-K. Tian, Chem. Commun. 2008, 1249-1251;
  • 14
    • 58449097152 scopus 로고    scopus 로고
    • 1H NMR spectral analysis.
    • 1H NMR spectral analysis.
  • 15
    • 58449132686 scopus 로고    scopus 로고
    • For the reaction of dibenzylic amine derivatives with highly activated arenes or heteroarenes, see ref, 3a and 3b
    • For the reaction of dibenzylic amine derivatives with highly activated arenes or heteroarenes, see ref. [3a and 3b].
  • 16
    • 33744802336 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: a) S. F. Kirsch, Org. Biomol. Chem. 2006, 4, 2076-2080;
    • (2006) Org. Biomol. Chem , vol.4 , pp. 2076-2080
    • Kirsch, S.F.1
  • 18
    • 13744249187 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 850-852.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 850-852
  • 19
    • 0001176061 scopus 로고    scopus 로고
    • For a review, see:, Eds, A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Pergamon Press, Oxford
    • For a review, see: B. A. Keay, P. W. Dibble in Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, Vol. 2, pp. 395-436.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 395-436
    • Keay, B.A.1    Dibble, P.W.2
  • 20
    • 58449122615 scopus 로고    scopus 로고
    • 2 alone nor TMSCl alone was able to catalyze the cycloisomerization of β-alkynyl diketone 3na.
    • 2 alone nor TMSCl alone was able to catalyze the cycloisomerization of β-alkynyl diketone 3na.
  • 21
    • 58449084220 scopus 로고    scopus 로고
    • 2 and 50 mol % of TMSCl at 70°C resulted in formation of benzofuran 4nj in 75 % yield.
    • 2 and 50 mol % of TMSCl at 70°C resulted in formation of benzofuran 4nj in 75 % yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.