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Ni(ii)/BINOL-catalyzed alkenylation of unactivated C(sp)-H bonds

Chemical Communications, ISSN: 1364-548X, Vol: 51, Issue: 37, Page: 7899-7902
2015
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Article Description

The first nickel-catalyzed alkenylation of unactivated C(sp)-H bonds with vinyl iodides is described. The catalytic system comprises an inexpensive and air-stable Ni(acac) as the catalyst and BINOL as the ligand, which is highly efficient for the alkenylation of β-methyl C(sp)-H bonds of a broad range of aliphatic carboxamides. The resulting olefins can serve as versatile handles for further preparation. Additionally, we also demonstrated the synthesis of functionalized carboxamides bearing α-quaternary carbon centers from simple pivalamide via nickel-catalyzed sequential C(sp)-H bond functionalization.

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