A Highly Efficient Method for the Reductive Etherification of Carbonyl Compounds with Triethylsilane and Alkoxytrimethylsilane Catalyzed by Iron(III) Chloride

Abstract

Facile reductive etherification of carbonyl compounds can be conveniently performed by reaction with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride. The corresponding alkyl ethers, including benzyl and allyl ethers, of the reduced alcohols were obtained in good to excellent yields under mild reaction conditions.

Key words

reductive etherification - iron(III) chloride - alkoxytri­methylsilane - triethylsilane - carbonyl compounds

References

• 1 Greene TW. Wuts PGM. In Protective Groups in Organic Synthesis   3rd ed.:  John Wiley & Sons; New York: 1999.  p.76 
• 2 Watahiki T. Akabane Y. Mori S. Oriyama T. Org. Lett.  2003,  5:  3045 
• 3 Kato J. Iwasawa N. Mukaiyama T. Chem. Lett.  1985,  743 
• 4a Sassaman MB. Kotian KD. Surya Prakash GK. Olah GA. J. Org. Chem.  1987,  52:  4314 
• 4b Hartz N. SuryPrakash GK. Olah GA. Synlett  1992,  569 
• 5 Hatakeyama S. Mori H. Kitano K. Yamada H. Nishizawa M. Tetrahedron Lett.  1994,  35:  4367 
• 6 Komatsu N. Ishida J. Suzuki H. Tetrahedron Lett.  1997,  38:  7219 
• 7 Yang W.-C. Lu X.-A. Kulkarni SS. Hung S.-C. Tetrahedron Lett.  2003,  44:  7837 
• 8 Chandrasekhar S. Chandrashekar G. Nagendra Babu B. Vijeender K. Venkatram Reddy K. Tetrahedron Lett.  2004,  45:  5497 
• 9 Torii S. Takagishi S. Inokuchi T. Okumoto H. Bull. Chem. Soc. Jpn.  1987,  60:  775 
• 10 Suzuki T. Ohashi K. Oriyama T. Synthesis  1999,  1561 
• 11 Sajiki H. Hirota K. Tetrahedron  1998,  54:  13981 
• 12 Alonso F. Barba I. Yus M. Tetrahedron  1990,  46:  2069 
• 13 Sarmah BK. Barua NC. Tetrahedron  1991,  47:  8587 
• 14 Ochiai M. Ito T. Takahashi H. Nakanishi A. Toyonari M. Sueda T. Goto S. Shiro M. J. Am. Chem. Soc.  1996,  118:  7716 
• 15 Akiyama T. Hirofuji H. Ozaki S. Bull. Chem. Soc. Jpn.  1992,  65:  1932 
• 16 Dinnocenzo JP. Zuilhof H. Lieberman DR. Simpson TR. McKechney MW. J. Am. Chem. Soc.  1997,  119:  994 
• 17 Kopechy DJ. Rychnovsky SD. J. Org. Chem.  2000,  65:  191