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Brown hydroboration

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Abstract

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

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References

  1. Brown, H. C.; 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.

    Google Scholar 

  2. Nussim, M.; Mazur, Y.; Sondheimer, F. J. Org. Chem. 1964, 29, 1120–1131.

    Article  Google Scholar 

  3. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents, Academic Press: New York, 1972. (Book).

    Google Scholar 

  4. Brewster, J. H.; Negishi, E. Science 1980, 207, 44–46. (Review).

    Google Scholar 

  5. Fu, G. C.; Evans, D. A.; Muci, A. R. Advances in Catalytic Processes 1995, 1, 95–121. (Review).

    Google Scholar 

  6. Hayashi, T. Comprehensive Asymmetric Catalysis I–III 1995, 1, 351–364. (Review).

    Google Scholar 

  7. Carter K. D.; Panek J. S. Org. Lett. 2004, 6, 55–57.

    Article  CAS  Google Scholar 

  8. Clay, J. M.; Vedejs, E. J. Am. Chem. Soc. 2005, 127, 5766–5767.

    Article  CAS  Google Scholar 

  9. Clay, J. M. Brown hydroboration reaction. In Name Reactions for Functional Group Transformations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2007, pp 183–188. (Review).

    Google Scholar 

  10. Smith, S. M.; Thacker, N. C.; Takacs, J. M. J. Am. Chem. Soc. 2008, 130, 3734–3735.

    Article  CAS  Google Scholar 

  11. Anderson, L. L.; Woerpel, K. A. Org. Lett. 2009, 11, 425–428.

    Article  CAS  Google Scholar 

  12. Yadav, J. S.; Kavita, A.; Raghavendra Rao, K. V.; Mohapatra, D. K. Tetrahedron Lett. 2013, 54, 1710–1713.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry College of Arts and Sciences, University of San Francisco, San Francisco, CA, USA

    Jie Jack Li

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  1. Jie Jack Li
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Li, J.J. (2014). Brown hydroboration. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_40

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