Science of Synthesis

Matteson, D. S., Science of Synthesis, (2005) 6, 18.

Sulfanylhydroboranes, compounds containing trigonal boron and the linkage R1—S—B—H, have not been used in synthesis beyond the academic exploration of their properties. There is no reason to expect that they would be advantageous in transition-metal-catalyzed processes, and the effort of preparing them and dealing with their odor has discouraged other applications. However, the use of 1,3,2-dithiaborolane as a hydroborating agent has been reported.[‌66‌] Sulfur does not interact nearly as strongly with the p-orbital of boron as does oxygen, and the result is that the boron atom is considerably more acidic. Consequently, 1,3,2-dithiaborolane is a faster hydroborating agent than catecholborane, and reacts readly with alkenes at 50°C.

References

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• 8.Meeeee-Meee, (8888) 8/8, 888.
• 8.Meeeee-Meee, (8888) 88/8e, 888.