Hydroboration Essay

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Amine Directed Hydroboration: Methodology and Synthetic Application Rebecca A. Murphy Department of Chemistry, University of California, Berkeley, California 94720 United States rmurphy@berkeley.edu ABSTRACT Directed hydroboration has been a topic of interest to practitioners of chemical synthesis for over fifty years. With recent advances in amine directed hydroboration, the field has gained momentum by being featured a series of methodological developments and natural product syntheses. In this paper, we highlight the advances made over this time period, as well as discuss recent applications to natural product synthesis. The discovery of hydroboration by H. C. Brown in 1959 sparked frenzied interest in the field of organoboron chemistry.1 Since this initial discovery, organoboron chemistry has become a mainstay in organic synthesis, and continues to be an important tool. A testament to this are the multiple Nobel prizes awarded for research in this area. In 2010, over 30 years after Brown’s Nobel prize for hydroboration chemistry, a Nobel prize was awarded to Akira Suzuki for his use of organoboron reagents in cross coupling reactions.2 The continued importance of organoborons is in part because they are highly versatile, and used for a wide range of chemical transformations (Scheme 1). Boronic acids, boronic esters, and boranes are available through the hydroboration of alkenes. They can subsequently be oxidized to give an alcohol3 or amine,4 or converted to the potassium trifluoroborate salt for use in a Suzuki-Miyaura cross coupling reaction.5 Also useful is hydroboration with 9-Borabicyclo[3.3.1]nonane (9-BBN), to give an organoborane that can also be used in a modified Suzuki reaction. Cross coupling reactions with trifluoroborate salts and 9-BBN organoboranes are of (1) Subba Rao, B. C.; Brown, H. C. J. Am. Chem. Soc. 1959, 81, 6423. (2) Suzuki, A.

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