Iodine‐Promoted Sulfenylation of Isoquinolinones

  • Author: European Journal of Organic Chemistry
  • Published Date: 07 January 2021
  • Copyright: Wiley-VCH GmbH
thumbnail image: Iodine‐Promoted Sulfenylation of Isoquinolinones

Related Societies

Isoquinolinones, a class of aromatic N-heterocycles, are often found in natural products and bioactive molecules. Straightforward synthetic access to functionalized isoquinolin-1(2H)-ones is, thus, useful. Different functional groups have been introduced into the C3/C4/C8 positions using transition-metal-catalyzed C–H functionalizations.

Guo-Li Huang, Yunnan Normal University, Kunming, China, and colleagues have developed a metal-free, green, simple, and efficient iodine-promoted method for the synthesis of 4-arylthioisoquinolin-1(2H)-ones under solvent-free conditions. The team used inexpensive and commercially available aryl sulfonyl chlorides as the sulfur source. Iodine (I2) and diethyl phosphite ((EtO)2P(O)H) allow the generation of electrophilic ArSI species, which can be converted to ArS· radical intermediates by homolysis. These intermediates can couple with the substrate and form the desired products.


The reaction proceeds smoothly in air and gives moderate to good yields of the C-4 sulfenylated products. The process has high regioselectivity, a broad substrate scope, and good functional group tolerance. Overall, the method provides simple, time-efficient, scalable, and low-cost access to 4-arylthio-substituted isoquinolin-1(2H)-one derivatives.



Article Views: 1481

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH