Synthesis 2016; 48(09): 1359-1370
DOI: 10.1055/s-0035-1561572
paper
© Georg Thieme Verlag Stuttgart · New York

Trimethylchlorosilane-Mediated Mild α-Chlorination of 1,3-Dicarbonyl Compounds Promoted by Phenyliodonium Diacetate

Siying Chong
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Yingpeng Su*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Lili Wu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Weigang Zhang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Junyan Ma
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Xiaowei Chen
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Danfeng Huang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Ke-Hu Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Yulai Hu*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: suyp51@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 18 November 2015

Accepted after revision: 01 February 2016

Publication Date:
02 March 2016 (online)


Abstract

Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature. The reaction allows the selective synthesis of α-monochlorinated products from different kinds of 1,3-dicarbonyl compounds in good yield. The potential possibility of this conversion for bromination has also been investigated.

Supporting Information

 
  • References

    • 1a De Kimpe N, Verhé R, Patai S. The Chemistry of α-Haloketones, α-Haloaldehydes, and α-Haloimines. In The Chemistry of Functional Groups. Patai S, Rappoport Z. John Wiley & Sons; Chichester: 1988
    • 1b Larock RC. Comprehensive Organic Transformations . 2nd ed. Wiley; New York: 1999: 716
    • 1c Thomas GX. Medicinal Chemistry: An Introduction . 2nd ed. John Wiley & Sons; Chichester: 2011
    • 1d Tilstam U, Weinmann H. Org. Process Res. Dev. 2002; 6: 384
    • 1e House HO. Modern Synthetic Reactions . 2nd ed. W. A. Benjamin; New York: 1972: 459
    • 2a Dowd P, Kaufman C, Kaufman P. J. Org. Chem. 1985; 50: 882
    • 2b Hakam K, Thielmann M, Thielmann T, Winterfeldt E. Tetrahedron 1987; 43: 2035
    • 3a Meshram HM, Reddy PN, Vishnu P, Sadashiv K, Yadav JS. Tetrahedron Lett. 2006; 47: 991
    • 3b Das B, Venkateswarlu K, Mahender G, Mahender I. Tetrahedron Lett. 2005; 46: 3041
    • 3c Wang C, Tunge J. Chem. Commun. 2004; 2694
    • 3d Tanemura K, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T. Chem. Commun. 2004; 470
    • 3e Yang D, Yan Y.-L, Lui B. J. Org. Chem. 2002; 67: 7429
    • 4a Rao AV. R, Singh AK, Reddy KM, Ravikumar K. J. Chem. Soc., Perkin Trans. 1 1993; 3171
    • 4b Shi X, Dai L. J. Org. Chem. 1993; 58: 4596
    • 5a Klimczyk S, Huang X, Fares C, Maulide N. Org. Biomol. Chem. 2012; 10: 4327
    • 5b Zav’yalov SI, Sitkareva IV, Ezhova GI. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1992; 41: 356
    • 5c Fraser RR, Kong F. Synth. Commun. 1988; 18: 1071
    • 6a Akula R, Galligan M, Ibrahim H. Chem. Commun. 2009; 6991
    • 6b Kim J.-J, Kweon D.-H, Cho S.-D, Kim H.-K, Lee S.-G, Yoon Y.-J. Synlett 2006; 194
    • 6c Khan AT, Goswami P, Choudhury LH. Tetrahedron Lett. 2006; 47: 2751
    • 6d Lee JC, Park JY, Yoon SY, Bae YH, Lee SJ. Tetrahedron Lett. 2004; 45: 191
    • 6e Ibrahim H, Akula R, Galligan M. Synthesis 2011; 347
    • 7a Varvoglis A. Hypervalent Iodine in Organic Synthesis . Academic Press; London: 1997
    • 7b Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
    • 7c Wirth T. Top. Curr. Chem. 2003; 224: 1-248
    • 7d Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656
    • 7e Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
    • 7f Zhdankin VV. ARKIVOC 2009; (i): 1
    • 7g Brand JP, Gonzalez DF, Nicolai S, Waser J. Chem. Commun. 2011; 47: 102
    • 7h Merritt EA, Olofsson B. Synthesis 2011; 517
    • 7i Yusubov MS, Nemykin VN, Zhdankin VV. Tetrahedron 2010; 66: 5745
    • 7j Satam V, Harad A, Rajule R, Pati H. Tetrahedron 2010; 66: 7659
  • 8 Narayan R, Manna S, Antonchick AP. Synlett 2015; 26: 1785
  • 9 Hara S, Sekiguchi M, Ohmori A, Fukuhara T, Yoneda N. Chem. Commun. 1996; 1899
    • 10a Turner TC, Shibayama K, Boger DL. Org. Lett. 2013; 15: 1100
    • 10b Shneider OS, Pisarevsky E, Fristrup P, Szpilman AM. Org. Lett. 2015; 17: 282
  • 11 Galligan MJ, Akula R, Ibrahim H. Org. Lett. 2014; 16: 600
  • 12 Sai Prathima P, Bikshapathi R, Rao VJ. Tetrahedron Lett. 2015; 56: 6385
  • 13 Tao J, Tuck TN, Murphy GK. Synthesis 2016; 48: 772
    • 14a Jia Z, Galvez E, Sebastian RM, Pleixats R, Alvarez-Larena A, Martin E, Vallribera A, Shafir A. Angew. Chem. Int. Ed. 2014; 53: 11298
    • 14b Boutillier P, Zard SZ. Chem. Commun. 2001; 1304