TTMSS Tris silane

Heteropolycyclic compounds were obtained [29] by treating bromo furylethers with tris-(trimethylsilyl)silane (TTMSS) in hot toluene containing a catalytic amount of AIBN (Equation 1.12). 

Natural products containing a spiropyrrolidinyloxindole nucleus have recently found to exhibit interesting biological activity such as cell-cycle inhibition [23]. This observation encouraged Murphy and coworkers to design a novel domino route to ( )-horsfiline (3-43), a natural spiropyrrolidinyloxindole (Scheme 3.13) [24]. Treatment of azide 3-39 with tris(trimethylsilyl)silane (TTMSS) and AIBN as radical starter led to the radical intermediate 3-40 after a first ring closure, which under-... 

Tricyclic derivative 186 was obtained by treating solution of 184 with tris(trimethylsilyl)silane (TTMSS) and azobisisobutyronitrile (AIBN). The pyridyl radical 185 is the suggested intermediate product (Scheme 4)... 

The same research group has further performed radical carbonylation reactions on the same microreactor system [36]. First, alkyl halides were initiated and effectively reacted with pressurized carbon monoxide to form carbonyl compounds. The principle was subsequently successfully extrapolated to the multicomponent coupling reactions. 1-Iodooctane, carbon monoxide and methyl vinyl ketone were reacted in the presence of 2,2 -azobis(2,4-dimethylvaleronitrile) (V-65) as an initiator and tributyltin hydride or tris(trimethylsilyl)silane (TTMSS) as catalyst (Scheme 15). 

Generation of 3-indolylacyl radicals from the selenoesters 149, using either /j-Bu3SnH or tris(trimethylsilyl)silane (TTMSS) followed by reaction with various alkenes, offers a route to 3-acylindoles 150. On the other hand, the use of n-Bu Sn2 under irradiation gave cyclopent[6]indole derivatives such as 151 via a cascade involving initial addition of the acyl radical to the alkene, and a subsequent oxidative cyclization at the indole C-2 <02JOC6268>. 

Chatgilialoglu and Curran have found that allyltris(triniethylsilyl)silanes react with a variety of alkyl halides to provide allylation products via an Sh2 process mediated by the tris(trimethylsilyl)silyl (TTMSS) radical (Scheme 10.199) [523]. In this system the allylsilanes work as radical-allylating agents and TTMSS radical sources. We have used the reactivity of allyltris(trimefhylsilyl)silanes for allylsilyla-tion of alkenes and alkynes via a radical chain mechanism (Scheme 10.199) [524]. 

Sultams can also be accessed by intramolecular cyclization of compounds containing preformed C-S-N-C-C fragments with a C-C bond formation as demonstrated in a one-pot synthesis of tricyclic sultam 236 <05SL577>. Tetrahydropyridine 235, obtained from 77,7/-bis(allyl)sulfonamide 234 by ring-closure-metathesis (RCM) followed by isomerization, undergoes radical cyclization in the presence of tris(trimethylsilyl)silane (TTMSS) to give tricycle sultam 236. 

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

Reactions of thiol esters with the three most commonly used reagents - tri-butylstannane,tris(trimethylsilyl)silane (TTMSS),and allyltributylstannane -were conducted using AIBN as an initiator. The reaction of 36 with 1.3 equiv of Bu3SnH in refluxing benzene with AIBN for 1 h led to complete consumption of the substrate and clean formation of the cyclization and reduction products (39 and 40, respectively, see Fig. 3) in a ratio of 96 4. As anticipated, dihydro-benzothiophene 41 was also formed in this reaction. It is worth noting that 40... 

TIPS triisopropylsilyl TTMSS recognition tris(trimethylsilyl)silane... 

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