Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis
Name
Jamison_Highly Regioselective.pdf
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1.02 MB
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Author(s)
Tasker, Sarah Zinnen
Jamison, Timothy F
Date Issued
August 2015
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Tasker, Sarah Z. and Jamison, Timothy F. “Highly Regioselective Indoline Synthesis Under Nickel/Photoredox Dual Catalysis.” Journal of the American Chemical Society 137, 30 (August 2015): 9531–9534 © 2015 American Chemical Society
Version
Author's final manuscript
Abstract
Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C–N bond-forming reductive elimination, producing a Ni(I) complex, which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox catalysts as controlled single electron transfer agents in multioxidation state nickel catalysis.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/jacs.5b05597
