Journal of Organic Chemistry p. 439 - 445 (1986)
Update date:2022-08-12
Topics:
Brown, Herbert C.
Prasad, J. V. N. Vara
Zee, Sheng-Hsu
The hydroboration of representative heterocyclic compounds bearing a vinyl or propenyl substituent with borane-methyl sulfide (BMS), 9-borabicyclo<3.3.1>nonane (9-BBN), dicyclohexylborane (Chx2BH), and disiamylborane (Sia2BH) was investigated systematically to establish directive effects in the hydroboration.The directive effects observed for 2-vinylfuran and 2-vinylthiophene are similar to those realized in styrene.The hydroboration of vinylpyridine required an excess of borane hydroborating agent.Alternatively, the nitrogen atom could be protected by complexing with boron trifluoride.When the vinyl group is ortho or para to the pyridine nitrogen, α-organoboranes are the major products in the hydroboration.However, when the vinyl group is meta to the pyridine nitrogen, β-organoboranes are formed predominantly.Hydroboration of the vinyl-pyridine-BF3 complexes results in an increase in the formation of α-organoboranes, as compared to β.The distribution of boron in the hydroboration of 2-propenyl heterocyclic compounds compared to that of trans-1-propenylbenzene showed that the effect of the heterocycle is pronounced in directing the boron atom strongly to the α-carbon atom.
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