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Volumn 13, Issue 4, 2011, Pages 656-659

Regioselective alkylation of heteroaromatic compounds with 3-methyl-2-quinonyl boronic acids

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EID: 79951615064     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1028964     Document Type: Article
Times cited : (19)

References (28)
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  • 2
    • 0001586671 scopus 로고
    • Friedel-Crafts Alkylations
    • Trost B.M. Fleming I. and, Eds.; Pergamon Press: Oxford
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    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293-339
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  • 3
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    • Trost B.M. Fleming I. and, Eds.; Pergamon: Oxford
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  • 5
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    • For recent reviews on asymmetric Friedel-Crafts reactions, see:;
    • For recent reviews on asymmetric Friedel-Crafts reactions, see: Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903-2915
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    • Poulsen, T.B.1    Jørgensen, K.A.2
  • 11
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    • For examples of protic acid catalyzed FC reaction, see:;
    • For examples of protic acid catalyzed FC reaction, see: Pirrung, M. C.; Park, K.; Li, Z. Org. Lett. 2001, 3, 365-367
    • (2001) Org. Lett. , vol.3 , pp. 365-367
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  • 14
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    • For a direct FC alkenylation in water without any added catalyst, see:;
    • For a direct FC alkenylation in water without any added catalyst, see: Zhan, H.-B.; Liu, L.; Chen, Y.-J.; Wang, D.; Li, C.-J. Eur. J. Org. Chem. 2006, 869-873
    • (2006) Eur. J. Org. Chem. , pp. 869-873
    • Zhan, H.-B.1    Liu, L.2    Chen, Y.-J.3    Wang, D.4    Li, C.-J.5
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    • Water is generated from the boronic acid/boroxine equilibrium presumably occurring in situ; see:;
    • Water is generated from the boronic acid/boroxine equilibrium presumably occurring in situ; see: Snyder, H. R.; Konecky, M. S.; Lennarz, W. J. J. Am. Chem. Soc. 1958, 80, 3611-3615
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3611-3615
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    • 3, to give, under similar reaction conditions, compound 10 in very different yields; see:, and ref 3c. We repeated both reactions under the conditions reported in both references to obtain a mixture of the starting 2-methylnaphthoquinone and the 1,4-addition product 10 (minor) in an 82:18 and a 96:4 ratio, respectively
    • 3, to give, under similar reaction conditions, compound 10 in very different yields; see: Reddy, A. V.; Ravinder, K.; Goud, T. V.; Krishnaiah, P.; Raju, T. V.; Venkateswarlu, Y. Tetrahedron Lett. 2003, 44, 6257-6260 and ref 3c. We repeated both reactions under the conditions reported in both references to obtain a mixture of the starting 2-methylnaphthoquinone and the 1,4-addition product 10 (minor) in an 82:18 and a 96:4 ratio, respectively
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6257-6260
    • Reddy, A.V.1    Ravinder, K.2    Goud, T.V.3    Krishnaiah, P.4    Raju, T.V.5    Venkateswarlu, Y.6
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    • See Supporting Information for details.
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.