Bidentate auxiliary-directed alkenyl C–H allylation via exo-palladacycles: synthesis of branched 1,4-dienes
2019
Shen, Cong | Lu, Xiunan | Zhang, Jian | Ding, Liyuan | Sun, Yaling | Zhong, Guofu
An alkenyl C–H allylation by an exo-palladacycle intermediate is demonstrated, employing unactivated (Z)-alkenes and allyl carbonates. With the use of an 8-aminoquinoline (AQ) derived amide as the directing group, the N,N-bidentate-chelation-assisted C–H activation protocol proceeded under mild and oxidant-free conditions with excellent selectivity. The utility of this approach is demonstrated by the preparative scale, selective conversion of inseparable Z/E alkenes and ready removal of the amide auxiliary to provide the corresponding ester.
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