Pd0-Catalysed C(sp3)-H Activation: From Direct to Remote Functionalization for the Construction of Medium-Sized Rings
In the context of the recent developments of palladium-catalysed C-H activation, the direct functionalization of C(sp3)-H bonds has proved to be a method of choice to access valuable building blocks. [1] [2] Taking advantage of this methodology, we recently proposed new direct functionalizations of C(sp3)-H bonds to access beta-lactams [3] and benzoxazines. [4]
In addition to direct functionalization, the ability of palladium to undergo a 1,4-through-space shift allows the functionalization of distal positions. [5] This interesting feature was combined with C(sp3)-H activation reaction on different systems, to access a wide range of gamma-lactams, indanones, benzofurans, chromanones and indolines. [6][7]
[1]: J. He, M. Wasa, K. S. L. Chan, Q. Shao, J. Q. Yu Chem. Rev. 2017, 117, 8754−8786
[2]: O. Baudoin, Acc. Chem. Res. 2017, 50, 1114-1123
[3]: D. Dailler, R. Rocaboy, Angew. Chem. Int. Ed., 2017, 56, 7218-7222
[4]: R. Rocaboy, D. Dailler. F. Zellweger, M. Neuburger, C. Salomé, E. Clot, O. Baudoin, Angew. Chem. Int. Ed., 2018, 10, 12131-12135
[5]: J.Q. Yu, Z. Shi, Top. Curr. Chem. 2010, 292, 123
[6]: R. Rocaboy, O. Baudoin, Org. Lett., 2019, 21, 1434–1437
[7]: R. Rocaboy, O. Baudoin, unpublished results