Visible-Light-Catalyzed C–C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3-Sulfonyl-1,2-dihydronaphthalenes

Abstract

A novel visible-light-catalyzed sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of CC bond sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond.

Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System

“…Visible light as renewable and clean energy has been widely used in synthetic chemistry and a variety of organic transformations can be achieved under very mild conditions. − In this context, ruthenium and iridium polypyridyl complexes are the most commonly employed photoredox catalysts. − Nevertheless, ruthenium and iridium are scarce metal elements; the cost and low sustainability of these noble-metal complexes are considered as major concerns of photoredox catalysis reaction. Thus, it is necessary to establish catalyst recycling/recovery technology for metal-based photoredox system.…”

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

“…Using Ru(bpy) 3 Cl 2 as photocatalyst, the visible-light-catalyzed sulfonylation/arylation of methylenecyclopropanes with sulfonyl chlorides for the synthesis of 3-sulfonyl-1,2-dihydro-naphthalenes was developed by Tang group. [83] A sequence of C=C bond sulfonylation, CÀ C σ-bond cleavage, and intramolecular cyclization were involved in the reaction mechanism. Sulfonyl radical was also generated from the oxidative quenching of the excited Ru(II)* with sulfonyl chlorides (Scheme 69).…”

Construction of Carbocycles from Methylenecyclopropanes

“…(72)] . Recently, a variety of reagents, such as AgSCF 3 , THF, aldehydes, sulfonyl chlorides, and sodium sulfinates found use to react with MCPs to construct the functionalized 3,4‐dihydronaphthalene skeletons via the catalytic or non‐catalytic free radical‐initiated cyclization reactions.…”