1,4-Bromoboration of nitroalkenes
Kanika Vashisth1, Caleb D Martin1
1Baylor University, Department of Chemistry and Biochemistry, One Bear Place #97348, Waco, TX 76798, USA. caleb_d_martin@baylor.edu.
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The selective 1,4-bromoboration of nitroalkenes occurs under mild conditions with a bromoborane featuring two 1-methyl-ortho-carborane substituents, BrBMeoCb2. The bromide is introduced on the β-carbon and the boryl moiety on the nitro group that is bound to boron in a κ2 manner. Screening a variety of other haloboranes gave either no reaction or indiscernible mixtures indicating the necessity for the BrBMeoCb2 reagent. The haloboration reaction tolerates a variety of aryl functional groups on the β-carbon as well as a hydrogen or methyl group on the α-carbon that all proceed with excellent regioselectivity and high isolated yields.
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