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Please login to access the full content or check if you have access via Method 6: The Barton–McCombie Deoxygenation of Alcohols Using Silanes as the Hydrogen-Atom Source

DOI: 10.1055/sos-SD-048-00072

Wicha, J.Science of Synthesis, (200948226.

Considerable attention has been devoted to the development of alternative hydrogen-atom donors and chain carriers for the BartonMcCombie reaction, which has been dominated by tin chemistry;[‌271‌‌273‌] for more information, see Section Organic silicon hydrides are capable of undergoing homolytic cleavage of the SiH bond and have little or no toxicity; they therefore form a broad group of potentially useful reducing agents. Several common alkyl- and arylsilanes have been evaluated for use as hydrogen-atom donors, and several silanes have been synthesized specifically for this purpose. The strength of the SiH bond in these silanes varies considerably, but even those with relatively strong SiH bonds can be used successfully.[‌274‌]