Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor–Acceptor Activation of Pyridinium Salts | Zendy

Jonathan A. Andrews | Zendy; Loïc Pantaine | Zendy; Christopher F. Palmer | Zendy; Darren L. Poole | Zendy; Michael C. Willis | Zendy

Open Access

Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor–Acceptor Activation of Pyridinium Salts

Author(s) -

Jonathan A. Andrews,

Loïc Pantaine,

Christopher F. Palmer,

Darren L. Poole,

Michael C. Willis

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c03194

Subject(s) - sulfonyl , chemistry , pyridinium , alkyl , radical , acceptor , electron acceptor , catalysis , salt (chemistry) , combinatorial chemistry , hydrogen atom , photochemistry , organic chemistry , physics , condensed matter physics

Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO 2 o generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.

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