Sulfenamide-enabled ortho thiolation of aryl iodides via palladium/norbornene cooperative catalysis

Renhe Li, Yun Zhou, Ki-Young Yoon, Zhe Dong () and Guangbin Dong ()
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Renhe Li: University of Chicago
Yun Zhou: University of Chicago
Ki-Young Yoon: University of Chicago
Zhe Dong: Merck Center for Catalysis at Princeton University
Guangbin Dong: University of Chicago

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract Poly-substituted aromatic sulfur compounds are widely found in pharmaceuticals, agrochemicals and organic materials. However, the position that a sulfur moiety can be introduced to is largely restricted to a pre-functionalized site; otherwise, use of electronically biased substrates or auxiliary groups that direct catalysis is required. Here we report a general ortho thiolation of common aryl and heteroaryl iodides via palladium-norbornene cooperative catalysis. Using this approach, an aryl or alky sulfur moiety can be site-selectively introduced at the arene ortho position without using sterically or electronically biased substrates. The arene ipso functionalization is simultaneously achieved through Heck, Suzuki or Sonogashira termination. The reaction is enabled by a unique class of electrophiles in palladium-norbornene cooperative catalysis, which are sulfenamides derived from seven-membered lactams. The broad substrates scope and high chemoselectivity could make this method attractive for synthesis of complex sulfur-containing aromatic compounds.

Date: 2019
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DOI: 10.1038/s41467-019-11398-0

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