化学
亚甲基
脱质子化
催化作用
选择性
分子内力
金属化
药物化学
表面改性
配体(生物化学)
立体化学
作者
Philip A. Provencher,John F. Hoskin,Jonathan L. Wong,Xiangyang Chen,Jin-Quan Yu,Kendall N. Houk,Erik J. Sorensen
摘要
Methylene-selective C-H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) catalysis. We report a Pd(II)-catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)-H arylation of ketones. The reaction utilizes glycine as a transient directing group and a 2-pyridone ligand, which may govern the methylene selectivity by making intimate molecular associations with the substrate during concerted metalation-deprotonation. This reaction is shown to be highly selective for intramolecular methylene C(sp3)-H arylation, thus enabling sequential C(sp3)-H functionalization.
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