BROWN Hydroboration

Addition of boranes to olefins followed by alkalinic oxidation of the organoborane adducts to afford alcohols. Regiochemistiy is anti-Markovnikov s rule. 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-O0, Springer International Publishing Switzerland 2014 

Tierney, P. A. J. Am. Chem. Soc. 1958, 80, 1552-1558. Herbert C. Brown (USA, 1912-2004) began his academic career at Wayne State University and moved on to Purdue University where he shared the Nobel Prize in Chemistry in 1981 with Georg Wittig (Germany, 1897-1987) for their development of organic boron and phosphorous compounds. 

Pelter, A. Smith, K. Brown, H. C. Bomne Reagents, Academic Press New York, 1972. (Book). 

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 35, Springer-Verlag Berlin Heidelberg 2009 

Brown hydroboration reaction. In Name Reactions for Functional Group Transformations, Li, J. J., Corey, E. J., Eds. Wiley Sons Hohoken, NJ, 2007 pp 183-188. (Review). 

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H. C. Brown, Hydroboration, W. A. Benjamin, Menlo Park, Calif., 1962. 

These last results combine the Wittig ylide chemistry with Brownes hydroboration reaction. We hope that a preparatively interesting ylide-borane chemistry will arise from this new "alloy". 

H. C. Brown, Hydroboration , Benjamin, New York, 1962 2nd printing with Nobel Lecture, Benjamin/Cummings, Reading, MA, 1980 H. C. Brown, Boranes in Organic Chemistry , Cornell University Press, Ithaca, NY, 1972. 

One of the most useful methods for preparing alcohols from alkenes is the hydroboration reaction reported in 1959 by H. C. Brown. Hydroboration involves addition of a B-H bond of borane, BH3, to an alkene to yield an organoborane intermediate, RBH2 ... 

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