Catalytic generation and use of ketyl radical from unactivated aliphatic carbonyl compounds
Name
acs.orglett.9b04235.pdf
Description
Published version
Size
1.14 MB
Format
Adobe PDF
Checksum (MD5)
db8efb5fd5030b6dd9327018b1d60c14
Author(s)
Seo, Hyowon
Jamison, Timothy F
Date Issued
December 2019
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Seo, Hyowon, and Timothy F. Jamison, "Catalytic generation and use of ketyl radical from unactivated aliphatic carbonyl compounds." Organic Letters 21, 24 (Dec. 2019): p. 10159-63 doi 10.1021/acs.orglett.9b04235 ©2019 Author(s)
Version
Final published version
Abstract
Generation of a ketyl radical from unactivated aliphatic carbonyl compounds is an important strategy in organic synthesis. Herein, catalytic generation and use of a ketyl radical for the reductive coupling of aliphatic carbonyl compounds and styrenes by organic photoredox catalysis is described. The method is applicable to both aliphatic ketones and aldehydes to afford the corresponding tertiary and secondary alcohols in continuous flow and batch. Preliminary mechanistic investigation suggests the catalytic formation of a ketyl radical intermediate.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology. Department of Chemical Engineering
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Creative Commons Attribution 4.0 International license
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.9b04235
