Ruthenium(II)-Catalyzed Remote C-H Sulfonylation of 2-Pyridones.

Authors :: Yang F
Zhou P
Huang Z
Liao J
Huang G
Liang T
Zhang Z
Source :: Organic letters [Org Lett] 2023 Aug 11; Vol. 25 (31), pp. 5779-5783. Date of Electronic Publication: 2023 Jul 27.
Publication Year :: 2023
Abstract: Herein, a ruthenium-mediated remote C-H mono- and disulfonylation of 2-pyridones with arylsulfonyl chlorides is developed. The catalytic system consisting of a [Ru( p -cymene)Cl <subscript>2</subscript> ] <subscript>2</subscript> catalyst and KOAc additive allows 2-pyridones to undergo C3,C5-disulfonylation in 1,4-dioxane, and C5-sulfonylation when the C3-position of 2-pyridones is blocked. The successful transformation of the products and late-stage modification of estrone further highlighted the potential utility and significance of this synthetic protocol. Preliminary mechanistic studies indicated that the remote regioselectivity might be dictated via chelation-assisted ruthenation.