Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)‒H Arylation with a Transient Directing Group

06 September 2021, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Methylene-selective C‒H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) cataly-sis. In this paper we report a Pd(II) catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)‒H arylation of ketones using a transient directing group. The reaction utilizes glycine as a transient directing group and an electron poor pyridone ligand which is expected to promote concerted metallation deprotonation, but also controls methylene selectivity by intimate interactions with the substrate. These reaction conditions are shown to be highly selective for in-tramolecular methylene C(sp3)‒H arylation, and thus enable sequential C(sp3)‒H functionalization.

Keywords

C-H Functionalization
Catalysis
Selective
Benzocyclobutene
Transient Directing Group
Palladium

Supplementary materials

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Description
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Supporting Information
Description
Compound characterization data for all new compounds and data for computations.
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