Room-Temperature C-H Bond Functionalization by Merging Cobalt and Photoredox Catalysis

Deepti Kalsi; Subhradeep Dutta; Nagaraju Barsu; Magnus Rueping; Basker Sundararaju

doi:10.1021/acscatal.8b02118

Room-Temperature C-H Bond Functionalization by Merging Cobalt and Photoredox Catalysis

Deepti Kalsi, Subhradeep Dutta, Nagaraju Barsu, Magnus Rueping, Basker Sundararaju^*

^*Corresponding author for this work

Chemistry

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

112 Scopus citations

Abstract

A non-noble metal-free protocol has been developed for C-H bond functionalization at room temperature by merging cobalt-mediated catalysis with photocatalysis. The reaction requires only oxygen as sole oxidant and operated at room temperature under redox-neutral conditions. Visible-light activated photoredox catalyst functions as an electron transfer reagent with oxygen as a terminal oxidant in the cobalt-mediated C-H and N-H bond annulation. The developed methodology allows annulations with various coupling partners. The concept demonstrated herein is expected to enhance the scope of cobalt catalysis as applied to sustainable fine chemical synthesis.

Original language	English (US)
Pages (from-to)	8115-8120
Number of pages	6
Journal	ACS Catalysis
Volume	8
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.8b02118
State	Published - Sep 7 2018

Bibliographical note

Funding Information:
Financial support provided by SERB (EMR2016/000136) to carry out this work is gratefully acknowledged. D.K., B.S., and M.R. thank DST-DAAD (DST/INT/FRG/DAAD/P-06/201) for Indo-German exchange program. D.K. and N.B. thank IITK and CSIR for their fellowship. The PK Kelkar Young Faculty Award to B.S. is gratefully acknowledged.

Publisher Copyright:
© 2018 American Chemical Society.

Keywords

amide
annulation
C-H bond functionalization
cobalt
photocatalysis
room temperature

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.8b02118

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title = "Room-Temperature C-H Bond Functionalization by Merging Cobalt and Photoredox Catalysis",

abstract = "A non-noble metal-free protocol has been developed for C-H bond functionalization at room temperature by merging cobalt-mediated catalysis with photocatalysis. The reaction requires only oxygen as sole oxidant and operated at room temperature under redox-neutral conditions. Visible-light activated photoredox catalyst functions as an electron transfer reagent with oxygen as a terminal oxidant in the cobalt-mediated C-H and N-H bond annulation. The developed methodology allows annulations with various coupling partners. The concept demonstrated herein is expected to enhance the scope of cobalt catalysis as applied to sustainable fine chemical synthesis.",

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author = "Deepti Kalsi and Subhradeep Dutta and Nagaraju Barsu and Magnus Rueping and Basker Sundararaju",

note = "Funding Information: Financial support provided by SERB (EMR2016/000136) to carry out this work is gratefully acknowledged. D.K., B.S., and M.R. thank DST-DAAD (DST/INT/FRG/DAAD/P-06/201) for Indo-German exchange program. D.K. and N.B. thank IITK and CSIR for their fellowship. The PK Kelkar Young Faculty Award to B.S. is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acscatal.8b02118",

language = "English (US)",

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AU - Kalsi, Deepti

AU - Dutta, Subhradeep

AU - Barsu, Nagaraju

AU - Rueping, Magnus

AU - Sundararaju, Basker

N1 - Funding Information: Financial support provided by SERB (EMR2016/000136) to carry out this work is gratefully acknowledged. D.K., B.S., and M.R. thank DST-DAAD (DST/INT/FRG/DAAD/P-06/201) for Indo-German exchange program. D.K. and N.B. thank IITK and CSIR for their fellowship. The PK Kelkar Young Faculty Award to B.S. is gratefully acknowledged. Publisher Copyright: © 2018 American Chemical Society.

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N2 - A non-noble metal-free protocol has been developed for C-H bond functionalization at room temperature by merging cobalt-mediated catalysis with photocatalysis. The reaction requires only oxygen as sole oxidant and operated at room temperature under redox-neutral conditions. Visible-light activated photoredox catalyst functions as an electron transfer reagent with oxygen as a terminal oxidant in the cobalt-mediated C-H and N-H bond annulation. The developed methodology allows annulations with various coupling partners. The concept demonstrated herein is expected to enhance the scope of cobalt catalysis as applied to sustainable fine chemical synthesis.

AB - A non-noble metal-free protocol has been developed for C-H bond functionalization at room temperature by merging cobalt-mediated catalysis with photocatalysis. The reaction requires only oxygen as sole oxidant and operated at room temperature under redox-neutral conditions. Visible-light activated photoredox catalyst functions as an electron transfer reagent with oxygen as a terminal oxidant in the cobalt-mediated C-H and N-H bond annulation. The developed methodology allows annulations with various coupling partners. The concept demonstrated herein is expected to enhance the scope of cobalt catalysis as applied to sustainable fine chemical synthesis.

KW - amide

KW - annulation

KW - C-H bond functionalization

KW - cobalt

KW - photocatalysis

KW - room temperature

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JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

Room-Temperature C-H Bond Functionalization by Merging Cobalt and Photoredox Catalysis

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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