Et3SiH

Indol-3-ylcarbinols can also be reduced using Et3SiH-TFA. Aryl indolyl-3-ylcarbinols can be formed in situ from 2-alkylindoles and benzaldehydes. These reactions, when run in tandem, provide a versatile route to 3-benzylin-doles[l 1]. Indole itself undergoes reduction to indoline under these conditions. lndol-3-ylcarbinols can also be generated by organomelallic additions to 3-acylindoles[12]. 

CF3COOH, CH2CI2, 25°, 1 h. The addition of Et3SiH to the deprotection step improves the yields over that obtained with the normal cation scavengers. ... 

TFA, CH2CI2, Et3SiH. Other scavengers are not nearly as effective, but when the xanthenyl group is used on a solid phase, more acid is required to get efficient cleavage. 

In 1971, a short communication was published [54] by Kumada and co-workers reporting the formation of di- and polysilanes from dihydrosilanes by the action of a platinum complex. Also the Wilkinson catalyst (Ph3P)3RhCl promotes hydrosilation. If no alkenes are present, formation of chain silanes occurs. A thorough analysis of the product distribution shows a high preference for polymers (without a catalyst, disproportionation reactions of the silanes prevail). Cross experiments indicate the formation of a silylene complex as intermediate and in solution, free silylenes could also be trapped by Et3SiH [55, 56],... 

Other reagents have also been used to reduce the C=0 of aldehydes and ketones to CH2. " Among these are Me3SiCl followed by Et3SiH/TiCl4, Ni(OAc)2 on... 

The carhonyl of acid derivatives can be reduced in some cases. Lactones are converted to cyclic ethers hy treatment with Cp2TiCl2 followed by Et3SiH on Amberlyst 15 .- - ... 

Though the usual product of epoxide reductions is the alcohol (10-85), epoxides are reduced all the way to the alkane by titanocene dichloride and Et3SiH-BH3. ... 

These reductions of lactols with Et3SiH 84b in combination of BE3 -OEt2, TfOH, or TMSOTf 20 have become standard reactions for synthesis of cyclic ethers [62-69]. Thus even co-hydroxyketones such as 1837 cyclize readily with excess EtsSiH 84b in the presence of TMSOTf 20, in high yields, via the lactols 1838, to give cyclic ethers such as the substituted oxepane 1839 in 90% yield [65] (Scheme 12.18). 

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