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RESEARCH ARTICLE

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Monobromoborane–Dimethyl Sulfide—a Highly Promising Reagent for the Regio- and Chemoselective Brominative Cleavage of Terminal Epoxides into Vicinal Bromohydrins*

Chandra D. Roy ^A ^B ^C and Herbert C. Brown ^A

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, IN 47907-2084, USA.

^B Current address: EMD Biosciences, Inc., 10394 Pacific Center Court, San Diego, CA 92121, USA.

^C Corresponding author. Email: chandra0919@gmail.com

Australian Journal of Chemistry 60(2) 139-145 https://doi.org/10.1071/CH06408
Submitted: 1 November 2006 Accepted: 3 December 2006 Published: 13 February 2007

Abstract

Monobromoborane–dimethyl sulfide (BH₂Br–SMe₂) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at –25°C, 4-chlorobenzaldehyde still underwent 12–13% reduction of an aldehydic group.

Acknowledgments

Financial supports from the Purdue Borane Research Fund and the Herbert C. Brown Center for Borane Research are gratefully acknowledged.

References

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^* This paper is dedicated to the memory of my mentor, the late Professor Herbert C. Brown (1912–2004). The work described herein was carried out at Purdue University during my stay as a post-doctoral research associate (1995–2001).