Synthesis and Applications - The Anderson Research Group

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Overview Introduction Synthesis of Alkenyl Silanes Alkynes Silyl Alkynes Terminal Vinyl Silanes Aldehydes Applications of Alkenyl Silanes Carbon-Oxygen Bond Formations Carbon-Carbon Bond Formations
Introduction SiR' 3 R Advantages of Alkenyl Silanes • behaves as latent functional groups unmasked through oxidation • activated under mild fluoride conditions • sufficiently stable to acid/base conditions and silica gel to carry through synthesis • relatively cheap and wide range of silyl precursors commercially available • organosilanes and reaction by-products are relatively non-toxic Disadvantages of Alkenyl Silanes Si-C bond lacks significant dipole and requires activation either by a heteroatom substituent or a fluoride source Types of Alkenyl Silane Substitution • all alkyl – TMS, TES, TBDMS etc. • oxygen – SiR n (OR) 3-n , SiMe 2 (OH), cyclic siloxanes • hydrogen • halides – fluoro, chloro • ‘safety-catch silanols’ – reveals silanol under fluoride or basic conditions Siletanes; Triallylsilanes; Dimethylbenzyl, phenyl, 2-pyridyl, 2-thienylsilanes
Page 1: Alkenyl Silanes - Synthesis and App
Page 5 and 6: Alkynes - Hydrosilylation Terminal
Page 7 and 8: Alkynes - Hydrosilylation Terminal
Page 9 and 10: Alkynes - Hydrosilylation Internal
Page 11 and 12: Alkynes - (Carbonylative) Silylcarb
Page 13 and 14: Silyl Alkynes Preparation of Silyl
Page 15 and 16: Silyl Alkynes - Hydrometallation Hy
Page 17 and 18: Silyl Alkynes - Carbometallation Al
Page 19 and 20: Synthesis of Alkenyl Silanes Alkyne
Page 21 and 22: Terminal Vinyl Silanes - Heck Coupl
Page 23 and 24: Synthesis of Alkenyl Silanes Alkyne
Page 25 and 26: Aldehyes - Peterson-Type Olefinatio
Page 27 and 28: Carbon-Oxygen Bond Formations Epoxi
Page 29 and 30: Carbon-Oxygen Bond Formations Tamao
Page 31 and 32: Applications of Alkenyl Silanes Car
Page 33 and 34: Carbon-Carbon Bond Formations Hiyam
Page 35 and 36: Carbon-Carbon Bond Formations Hiyam
Page 37 and 38: Carbon-Carbon Bond Formations Other
Page 39 and 40: Carbon-Carbon Bond Formations Cu(I)
Page 41: Thank you!

Synthesis and Applications - The Anderson Research Group

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