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Resolving a Reactive Organometallic Intermediate from Dynamic Directing Group Systems by Selective C-H Activation.

ABSTRACT: Catalyst discovery from systems of potential precursors is a challenging endeavor. Herein, a new strategy applying dynamic chemistry to the identification of catalyst precursors from C-H activation of imines is proposed and evaluated. Using hydroacylation of imines as a model reaction, the selection of an organometallic reactive intermediate from a dynamic imine system, involving many potential directing group/metal entities, is demonstrated. The identity of the amplified reaction intermediate with the best directing group could be resolved in situ by ESI-MS, and coupling of the procedure to an iterative deconvolution protocol generated a system with high screening efficiency.

SUBMITTER: Schaufelberger F

PROVIDER: S-EPMC5836886 | biostudies-other | 2018 Jan

REPOSITORIES: biostudies-other

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Resolving a Reactive Organometallic Intermediate from Dynamic Directing Group Systems by Selective C-H Activation.

Schaufelberger Fredrik F Timmer Brian J J BJJ Ramström Olof O

Chemistry (Weinheim an der Bergstrasse, Germany) 20171207 1

Catalyst discovery from systems of potential precursors is a challenging endeavor. Herein, a new strategy applying dynamic chemistry to the identification of catalyst precursors from C-H activation of imines is proposed and evaluated. Using hydroacylation of imines as a model reaction, the selection of an organometallic reactive intermediate from a dynamic imine system, involving many potential directing group/metal entities, is demonstrated. The identity of the amplified reaction intermediate w ...[more]

PMID: 29149517

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