Iron-Catalyzed Synthesis of Sulfur-Containing Heterocycles

Abstract

An iron-catalyzed synthesis of sulfur- and sulfone-containing heterocycles is reported. The method is based on the cyclization of readily available substrates and proceeded with high efficiency and diastereoselectivity. A variety of sulfur-containing heterocycles bearing moieties suitable for subsequent functionalization are prepared. Illustrative examples of such postcyclization modifications are also presented.

Introducing a sulfone-embedded anhydride to the anhydride-imine reaction for the modular synthesis of N-heterocyclic sulfones bearing vicinal stereocenters

“…2B ). 16 Inspired by the pharmaceutical relevance of sp 3 -rich N-heterocyclic sulfones, we sought to evaluate the performance of anhydride 6 in formal cycloaddition reactions featuring several imines such as 7 ( Fig. 2C ).…”

Iodine-promoted insertion of the oxygen atom from water in η4-vinylketene[Fe(CO)3] complexes

“…Today, iron-mediated catalysis has become a versatile tool for the construction of new bonds such as C–O, 1 C–S 2 and C–N. 3 Likewise, several catalytic methodologies involving iron species have been successfully used to perform Csp 2 –Csp 3 and Csp 3 –Csp 3 cross-couplings, including their enantioselective versions.…”

Facile preparation of dihydro-1,4-benzothiazine derivatives via oxidative ring-expansion of 2-aminobenzothiazoles with olefins

“…2,3 In particular, for the synthesis of dihydro-1,4-benzothiazine derivatives, Jiang and co-workers 4 developed a Pd-catalyzed double C–S bond coupling reaction to prepare substituted dihydro-1,4-benzothiazine derivatives, in which Na 2 S 2 O 3 was employed as a sulfur source to avoid a thiol odor (Scheme 1a). Cossy et al 5 described a FeCl 3 -catalyzed intramolecular nucleophilic cyclization to construct the 1,4-benzothiazine skeleton via a carbocation intermediate (Scheme 1b). Yi and co-workers 6 reported a radical involving annulation strategy to access 1,4-benzothiazine derivatives from feedstock of 2-aminobenzenethiols and ketones (Scheme 1c).…”