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Published on: May 21, 2019
Visible-light-driven cascade cyclization: a modular approach to functionalized 4-pyrrolin-2-ones
Rupashri Dash1, Karan Ramdas Thombare1, Anindya Das1
1Department of Chemistry, Indian Institute of Technology Jodhpur, Karwar-342037, Rajasthan, India. sandipmurarka@iitj.ac.in.
None:
We report an efficient and modular strategy for the construction of densely functionalized 4-pyrrolin-2-ones via visible-light-driven Ru(II) photocatalysis. The radical cascade cyclization approach enables the diversity-oriented synthesis of benzylated and alkylated 4-pyrrolin-2-one scaffolds, utilizing readily accessible diaryliodonium salts (DAIRs) and N-(acyloxy)phthalimides (NHPI esters) as radical precursors. The methodology is further expanded to include other radical coupling partners, such as trifluoromethyl and arylsulfonyl radicals, affording a wide array of structurally diverse and synthetically valuable 4-pyrrolin-2-ones. The protocol is characterized by its robustness, broad substrate scope, high functional group tolerance, and scalability, collectively underscoring its synthetic utility.
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