Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling was written by Porey, Sandip;Zhang, Xinglong;Bhowmick, Suman;Kumar Singh, Vikas;Guin, Srimanta;Paton, Robert S.;Maiti, Debabrata. And the article was included in Journal of the American Chemical Society in 2020.Product Details of 620-19-9 This article mentions the following:
The late-stage functionalization (LSF) of pharmaceutical and agrochem. compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chem. space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochems. with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and exptl. mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step. In the experiment, the researchers used many compounds, for example, 1-(Chloromethyl)-3-methylbenzene (cas: 620-19-9Product Details of 620-19-9).
1-(Chloromethyl)-3-methylbenzene (cas: 620-19-9) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Product Details of 620-19-9
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics