Journal
TETRAHEDRON
Volume 69, Issue 31, Pages 6448-6460Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.05.078
Keywords
LiNK metalation; Substituted benzyltrimethylsilanes; Benzyl anion equivalents
Categories
Funding
- European Research Association ERA-Chemistry
- Irish Research Council (IRC)
Ask authors/readers for more resources
The regioselective benzylic metalation of toluenes using BuLi/(KOBu)-Bu-t/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. ArCH2Si(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. (C) 2013 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available