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Poly(methylhydrosiloxane) is used in the reduction of esters to alcohols, catalyzed by a combination of titanocene dichloride and either n-BuLi or EtMgBr. It is a safer alternative to triethoxysilane, B22063, for reduction of phosphine oxides to phosphines, catalyzed by Ti(O-i-Pr)4. It is also used in greener amine synthesis by reductive amination as an alternative to borohydrides.
Bhanu P. S. Chauhan.; Rajesh Sardar. Self-Assembled Stable Silver Nanoclusters and Nanonecklace Formation:? Poly(methylhydrosiloxane)-Mediated One-Pot Route to Organosols. Macromolecules. 2004, 37 (14), 5136-5139.
Bhanu P.S. Chauhan.; Philip Boudjouk. New neutral carrier-type ion sensors. Crown ether derivatives of poly(methylhydrosiloxane). Tetrahedron Letters. 1999, 40 (22), 4123-4126.
Convenient reducing agent with a wide variety of applications, for example:
Reduction of esters to alcohols, catalyzed by a combination of titanocene dichloride and either n-BuLi or EtMgBr: J. Org. Chem., 59, 4323 (1994). Alternatively, in combination with Ti(O-i-Pr)4 reduces a variety of esters, generally in high yield: J. Org. Chem., 60, 7884 (1995); Synlett, 831 (1994). For one-step reductive amination of carbonyl compounds in similar fashion, see: Synlett, 1655 (2000). Reduction of esters, carboxylic acids, ketones and aldehydes can also be accomplished conveniently with TBAF as a catalyst: Synlett, 989 (1997). For asymmetric reduction of ketones catalyzed by chiral quaternary fluorides, see: Tetrahedron Lett., 38, 5857 (1997).
Low-cost, safer alternative to Triethoxysilane, B22063, for reduction of phosphine oxides to phosphines, catalyzed by Ti(O-i-Pr)4. The products may be reacted in situ with alkyl halides to give a convenient one-pot conversion of phosphine oxides to phosphonium salts: Tetrahedron Lett., 35, 625 (1994).
Amine N-oxides can be reduced in the presence of Ti(O-i-Pr)4 or Pd(0): Synlett, 349 (2002).
Pd(0)-catalyzed hydrogenolysis of alkyl and aryl halides: J. Org. Chem., 51, 734 (1986). Pd(0)-catalyzed reductive cyclization of 1,6- and 1,7-enynes to give exomethylene cyclopentanes and cyclohexanes: J. Am. Chem. Soc., 109, 3161 (1987).
Low-cost alternative to Triethylsilane, A10320, in a one-pot aromatic acylation-reduction technique allowing alkylation of the aromatic ring without the polysubstitution and rearrangements associated with Friedel-Crafts alkylations. Acylation in the presence of AlCl3 is followed by in situ reduction with PMHS: J. Chem. Soc., Perkin 1, 1705 (1989).
For a review of PMHS, see: J. Chem. Soc., Perkin 1, 3381 (1999).
Precautionary Statements: P260-P201-P280-P304+P340-P405-P501a
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