Mild and low-pressure fac-Ir(ppy)3-mediated radical aminocarbonylation of unactivated alkyl iodides through visible-light photoredox catalysis

Shiao Y. Chow; Marc Y. Stevens; Linda Åkerbladh; Sara Bergman; Luke R. Odell

doi:10.1002/chem.201601694

Mild and low-pressure fac-Ir(ppy)₃-mediated radical aminocarbonylation of unactivated alkyl iodides through visible-light photoredox catalysis

Shiao Y. Chow, Marc Y. Stevens, Linda Åkerbladh, Sara Bergman, Luke R. Odell^*

^*Corresponding author for this work

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)₃-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)₃, amines, reductants, and CO gas (released ex situ from Mo(CO)₆), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.

Original language	English
Pages (from-to)	9155-9161
Number of pages	7
Journal	Chemistry - A European Journal
Early online date	7 Jun 2016
DOIs	https://doi.org/10.1002/chem.201601694
Publication status	Published - 23 Jun 2016

Funding

This work was supported by the Carl Tryggers Foundation for Scientific Research (CTS13:333, CTS14:356) and Uppsala University. The authors thank Mr Magnus Fagrell (Fagrell Produktutveckling AB, Sweden) for help with pressure measurement studies and Dr Lisa D. Haigh (Imperial College London, U.K.) for assistance with accurate mass determination.

Keywords

amides
carbonylation
photocatalysis
radical reactions

Access to Document

10.1002/chem.201601694

Cite this

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title = "Mild and low-pressure fac-Ir(ppy)3-mediated radical aminocarbonylation of unactivated alkyl iodides through visible-light photoredox catalysis",

abstract = "A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.",

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AU - Chow, Shiao Y.

AU - Stevens, Marc Y.

AU - Åkerbladh, Linda

AU - Bergman, Sara

AU - Odell, Luke R.

PY - 2016/6/23

Y1 - 2016/6/23

N2 - A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.

AB - A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.

KW - amides

KW - carbonylation

KW - photocatalysis

KW - radical reactions

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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