Reduction of Carbonyl to Methylene: Organosilane-Ga(OTf)3
511
21. Gadhwal S, Baruah M, Sandhu JS (1999) Synlett 1573
22. Chandrasekhar S, Reddy CR, Babu BN (2002) J Org Chem
67:9080
(TfO)3Ga
(TfO)3Ga
SiMe2Cl
O
O
+
H SiMe2Cl
R
R'
R
R'
´
¨ ¨
23. Torok B, London G, Bartok M (2000) Synlett 631
24. Broome J, Brown BR, Roberts A, White AMS (1960) J Chem Soc
1406
H
3
1
(TfO)3Ga
SiMe2Cl
H
25. Zieger HE, Dixon JA (1960) J Am Chem Soc 82:3702
26. Brewster JH, Osman SF, Bayer HO, Hopps HB (1964) J Org
Chem 29:121
27. Satoh T, Mitsuo N, Nishiki M, Nanba K, Suzuki S (1981) Chem
Lett 1029
O
SiMe2Cl
+
+ (Me2ClSi)2O
R'
R
-Ga(OTf)3
H
R
R'
H
H
3
4
2
28. Suzuki H, Masuda R, Kubota H, Osuka A (1983) Chem Lett 909
29. Eisch JJ, Liu ZR, Boleslawski MP (1992) J Org Chem 57:2143
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31. Gribble GW, Leese RM (1977) Synthesis 172
´ ´ ´
32. Lau CK, Dufresne C, Belanger PC, Pietre S, Scheigetz J (1986) J
Org Chem 51:3038
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54:491
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(1995) Synlett 93
Scheme 2 Proposed Proposed reaction pathway for the Ga(OTf)3
catalyzed direct deoxygenation of ketones
contribute to the development of a sustainable strategy for
the synthesis of useful building blocks and bioactive
molecules.
Acknowledgments Financial support by Loker Hydrocarbon
Research Institute is gratefully acknowledged.
36. Dehmlow ED, Niemann T, Krafts A (1996) Synth Commun
26:1467
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