Metal-catalyzed hydroboration and diboration of thiocarbonyls and vinyl sulfides
CAG Carter, CM Vogels, DJ Harrison… - …, 2001 - ACS Publications
CAG Carter, CM Vogels, DJ Harrison, MKJ Gagnon, DW Norman, RF Langler, RT Baker…
Organometallics, 2001•ACS Publications… Although attempts to diborate thiocarbonyl compounds 1a−d proved unsuccessful using
a number of different metal catalysts, we have found that B 2 (cat) 2 adds to (1R)-(−)-thiocamphor
(4) in high yields using a catalytic amount of RhCl(PPh 3 ) 3 to give a single isomer of the
diborated product 6. Aqueous workup provided the corresponding thiol 7, but we have not
yet been able to deprotect the carbon-bound boryl group to the corresponding boronic acid (Figure
3). The reactions described here are the first examples of … In summary, we have found …
a number of different metal catalysts, we have found that B 2 (cat) 2 adds to (1R)-(−)-thiocamphor
(4) in high yields using a catalytic amount of RhCl(PPh 3 ) 3 to give a single isomer of the
diborated product 6. Aqueous workup provided the corresponding thiol 7, but we have not
yet been able to deprotect the carbon-bound boryl group to the corresponding boronic acid (Figure
3). The reactions described here are the first examples of … In summary, we have found …
α-Thioboronate esters are obtained directly in high yield and selectivity from metal-catalyzed additions of B−X bonds (X = H, B) to thiocarbonyl compounds and vinyl sulfides.
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