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Difluoroalkylation of tertiary amides and lactams by an iridium-catalyzed reductive Reformatsky reaction

05 November 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The synthesis of medicinally relevant α-difluoroalkylated amines by an iridium-catalyzed reductive alkylation of tertiary amides and lactams with difluoro-Reformatsky reagents, is described. This report features the introduction of various geminal difluoro-acetates and -acetamides as well as late stage derivatization of APIs, gram scale synthesis and downstream functionalizations.

Keywords

difluoroalkylation
tertiary amides
Reformatsky
iridium
C-C coupling

Supplementary materials

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Description
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Supporting information
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Full optimization details, synthesis and characterization of starting materials and products, NMR spectra of unknown compounds.
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Version History

Nov 05, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-269vx
D O I: 10.26434/chemrxiv-2021-269vx [opens in a new tab]

Funding

European Commission
892540

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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