School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, China.
Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055, China.
J Org Chem. 2023 Feb 17;88(4):2599-2604. doi: 10.1021/acs.joc.2c02697. Epub 2023 Jan 26.
Chemo- and site-selective functionalization of phenols offers a rapid strategy for the synthesis of phenol derivatives with diverse structures. Herein, we report a Pd-catalyzed regioselective C-H bond allylic alkylation of phenols with 1,3-dienes, which has precision reactivity at the C-H bond of 2-naphthols, 1-naphthols, and electron-rich phenols. The reaction is accelerated by a diphosphine ligand, does not need any other additive, and features broad substrate scope and good chemo- and regioselectivity. In addition, we have also investigated the asymmetric variant, and the product could be achieved in up to 55% ee.
酚的化学选择性和位点选择性功能化提供了一种快速合成具有不同结构的酚衍生物的策略。在此，我们报道了一种钯催化的酚与 1,3-二烯的区域选择性 C-H 键烯丙基烷基化反应，该反应在 2-萘酚、1-萘酚和富电子酚的 C-H 键上具有精准的反应活性。该反应由双膦配体加速，不需要任何其他添加剂，具有广泛的底物范围和良好的化学选择性和区域选择性。此外，我们还研究了不对称变体，产物的对映选择性最高可达 55%ee。
