Bu4N+ alkoxide-initiated/autocatalytic addition reactions with organotrimethylsilanes.
The use of Me3SiO(-)/Bu4N(+) as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.
Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland , 123 St. Stephen's Green, Dublin 2, Ireland.
Manas
M
Das
Donal F
DF
O'Shea
D002384:Catalysis; D002412:Cations / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D002412:Cations; D009942:Organometallic Compounds; D017646:Organosilicon Compounds; D000644:Quaternary Ammonium Compounds; D011807:Quinolizines; D013457:Sulfur Compounds; D014297:Trimethylsilyl Compounds; C438055:dithiane; C403764:tetrabutylammonium triphenyldifluorosilicate; C009405:tetrabutylammonium