71435-93-3Relevant academic research and scientific papers
Addition of N-Heterocyclic Carbene Catalyst to Aryl Esters Induces Remote C-Si Bond Activation and Benzylic Carbon Functionalization
Wang, Hongling,Chen, Xingkuan,Li, Yongjia,Wang, Jilan,Wu, Shuquan,Xue, Wei,Yang, Song,Chi, Yonggui Robin
supporting information, p. 333 - 336 (2018/01/28)
Through the incorporation of a silicon atom to an aryl carboxylic ester substrate, the resulting C-Si bond can be activated via the addition of a carbene catalyst on a remote site. This strategy allows for efficient functionalization of the benzylic sp3-carbons of aryl carboxylic esters.
Synthesis and application of benzyl-TMS derivatives as bench stable benzyl anion equivalents
Das, Manas,O'Shea, Donal F.
, p. 6448 - 6460 (2013/07/26)
The regioselective benzylic metalation of toluenes using BuLi/KO tBu/TMP(H) (LiNK metalation conditions) and subsequent transmetalation to Si by reaction with TMSCl provides a general one-pot procedure for the synthesis of substituted benzyltrimethylsilanes. ArCH 2Si(Me)3 derivatives are bench stable reagents yet can serve as benzyl anion equivalents under mild reaction conditions. Following activation with fluoride they can successfully participate in a wide range of additions to both non-enolizable and enolizable carbonyls. In addition, their use in the synthesis of isochromanones and trifluoromethylated amines is illustrated. The broad synthetic scope and mild practical conditions of use for ArCH2Si(Me)3 reagents demonstrate their general potential as benzyl anion equivalents.
THE PHOTOCHEMISTRY OF o-ACETOPHENONE
Bergmark, William R.,Meador, Michael,Isaacs, James,Thiim, Michael
, p. 1109 - 1111 (2007/10/02)
The title compound was prepared and irradiated under a variety of conditions to produce no change.Irradiation id DMSO-d6 and methanol-d4 results in D incorporation into the o-(trimethylsilyl)methyl group.Irradiation in 2-propanol results in photoreduction (φ=0.012) which could be quenched with dienes (kqτ=4.5).These results are taken to suggest a rapid, efficient, and reversible H-transfer with no detectable silyl transfer.
