Jonathan E. Wilson
Nov 16, 2016
Citations
0
Influential Citations
22
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The incorporation of a methyl group into a small molecule can have a profound impact on its biological activity, pharmacokinetic profile, and physical properties. As part of an ongoing effort to develop novel methods for methylation of small molecule drug candidates, a three-component coupling of aryliodides, O-benzoylamines, and methylboronic acid that proceeds via a Catellani-type mechanism has been developed. The methodology allows for the ortho-amination/ipso-methylation of aryl- and heteroaryliodides with a wide variety of cyclic O-benzoylamines including pyrrolidines, piperidines, piperazines, morpholines, azepines, diazepines, and azocanes in a single step. A preliminary result for an ortho-methylation/ipso-olefination Catellani-type three component-coupling reaction is also described.