Synlett 2009(9): 1445-1448  
DOI: 10.1055/s-0029-1216746
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Thioglycoluril as a Novel Organocatalyst: Rapid and Efficient α-Monobromination of 1,3-Dicarbonyl Compounds

Liping Cao, Jiaoyang Ding, Guodong Yin, Meng Gao, Yitao Li, Anxin Wu*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China
e-Mail: [email protected];
Further Information

Publication History

Received 10 January 2009
Publication Date:
04 May 2009 (online)

Abstract

Thioglycoluril as a novel hydrogen-bonding organocatalyst, combined with NBS, in MeOH provided rapid and efficient α-monobromination of 1,3-dicarbonyl compounds in excellent yields at room temperature. A bifunctional catalytic mechanism was proposed from these results.

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21

Crystal Data for Compound 1d C16H14N4S2, M = 326.43, orthorhombic, a = 11.153 (3), b = 8.0271 (19), c = 8.5859 (19) Å, α = 90.00˚, β = 90.00˚, γ = 90.00˚, V = 768.6 (3) ų, T = 298 (2) K, space group Pmn2 (1), Z = 2, µ(Mo Kα) = 0.347 mm, 4575 reflections measured, 1417 unique (R int = 0.0363) which were used in all calculations. The final wR 2 (F 2) was 0.1796 (all data). CCDC 708178 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; email: [email protected]].