In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Catalytic Direct Cyanomethylenation of C(sp3)-H Bonds via A One-Step Double C-C Bond Formation, published in , which mentions a compound: 6797-13-3, mainly applied to benzoxazolyl arylacrylonitrile diastereoselective preparation; arylmethyl benzoxazole DMF trimethylsilyl cyanide cyanomethylenation catalyst palladium copper; benzothiazolyl arylacrylonitrile diastereoselective preparation; benzothiazole arylmethyl DMF trimethylsilyl cyanide cyanomethylenation catalyst palladium copper; oxo aryl arylbutenenitrile diastereoselective preparation; aryl arylethanone DMF trimethylsilyl cyanide cyanomethylenation catalyst palladium copper, Application In Synthesis of 2-Ethylbenzo[d]oxazole.
An elegant and catalytic procedure for the one-step cyanomethylenation of C(sp3)-H bonds adjacent to benzazoles and ketones was described herein using DMF as a C-1 unit and TMSCN as the cyanide source. The copper mediated reaction between DMF and TMSCN gave a cyanomethylene radical intermediate that reacts with 2-alkylbenzazoles or alkylketones to furnish desired cyanomethylenated compounds I [R = Me, Ph, 4-MeOC6H4, etc.; R3 = H, 5-Cl, 6-Me, etc.; X = O, S] and II [R1 = Ph, 4-MeOC6H4, 4-BrC6H4 etc.; R2 = Ph, 4-BrC6H4, 4-O2NC6H4] under palladium catalysis. Subsequent interconversion of cyanomethylenated products I and II has made the protocol synthetically attractive.
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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem