Tris silane reducing agent

Lithium triethylborohydride reducing agent, mild nucleoside chemistry Tris (trimethylsilyl) silane reducing agent, mild reductive cleavage of cyclic ethers... 

Reduction by hydrogen atom donors involves free radical intermediates and usually proceeds by chain mechanisms. Tri-n-butylstannane is the most prominent example of this type of reducing agent. Other synthetically useful hydrogen atom donors include hypophosphorous acid, dialkyl phosphites, and tris-(trimethylsilyl)silane. The processes that have found most synthetic application are reductive replacement of halogen and various types of thiono esters. 

The combination of PhSiH3 with a catalytic amount of bis(tri-n-butyltin) oxide reduces azides to primary amines in excellent yields (Eq. 3 33).556 The reducing agent is (n-Bu)3SnH formed in situ by the silane. Azides are converted into Boc-protected primary amines with the PMHS/Pd/C reagent (Eq. 3 34).557,558... 

Tris(trimethylsilyl)silane is found to be an efficient reducing agent for a variety of functional groups. In particular, the reduction of halides, chalcogen groups, thiono esters and isocyanides are the most common ones. The efficiency of these reactions is also supported by available kinetic data. The rate constants for the reaction of (TMS)3Si radicals with a variety of organic substrates are collected in Table 2. 

Radical reactions with acyl radicals sometimes involve decarbonylation as side-reactions, especially when stabilized secondary or tertiary radicals can be formed. These side-reactions can be suppressed using low-temperature reaction conditions together with different reducing agents such as tris(trimethylsilyl)silane.254... 

Tris(trimethylsilyl)silane Historical Perspective and What Can Be Done 20 Years After its Discovery as a Radical-based Reducing Agent... 

Tris(trimethylsilyl)silane (TTMSS) reducing agent for alkyl halides, ketones an alternative to tributyltin hydride. 

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