Iridium-catalyzed alkenyl C-H allylation using conjugated dienes.

Chem Commun (Camb)

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China.

Published: August 2019

An iridium-catalyzed C-H allylation of acrylamides with conjugated dienes was developed, using NH-Ts amide as the directing group. The ligand- and additive-free protocol provided a convenient and atom economic synthesis of branched 1,4-diene skeletons, enabling the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF3. The utility of this protocol is also demonstrated by a preparative scale, as well as C-H functionalization of artemisic amide. Furthermore, NH-Ts amide was efficiently removed by methylation and hydrolysis procedures to provide 1,4-dienoic acid.

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http://dx.doi.org/10.1039/c9cc04419aDOI Listing

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