1037075-33-4Relevant academic research and scientific papers
Sulfonium-Based Homolytic Substitution Observed for the Radical SAM Enzyme HemN
Deng, Zixin,Ding, Wei,Ji, Wenjuan,Ji, Xinjian,Mandalapu, Dhanaraju,Sun, Peng,Zhang, Qi
, p. 8880 - 8884 (2020)
Sulfur-based homolytic substitution (SH reaction) plays an important role in synthetic chemistry, yet whether such a reaction could occur on the positively charged sulfonium compounds remains unknown. In the study of the anaerobic coproporphyrinogen III oxidase HemN, a radical S-adenosyl-l-methionine (SAM) enzyme involved in heme biosynthesis, we observed the production of di-(5′-deoxyadenosyl)methylsulfonium, which supports a deoxyadenosyl (dAdo) radical-mediated SH reaction on the sulfonium center of SAM. The sulfonium-based SH reactions were then investigated in detail by density functional theory calculations and model reactions, which showed that this type of reactions is thermodynamically favorable and kinetically competent. These findings represent the first report of sulfonium-based SH reactions, which could be useful in synthetic chemistry. Our study also demonstrates the remarkable catalytic promiscuity of the radical SAM superfamily enzymes.
Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature
Kim, Kicheol,Hong, Soon Hyeok
, p. 2345 - 2351 (2017/07/22)
The first photoinduced copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp2 cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to SN2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I) cyanide catalytic intermediate. (Figure presented.).
Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride
Sakai, Norio,Nakajima, Takumi,Yoneda, Shinichiro,Konakahara, Takeo,Ogiwara, Yohei
, p. 10619 - 10623 (2015/02/19)
Described herein is the direct chlorination of carboxylic acids using copper(II) chloride via a gallium(III)-catalyzed reduction in the presence of a hydrosiloxane. During this reductive chlorination, the counteranions of CuCl2 functioned as a chloride source.
Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction
Minatti, Ana,Buchwald, Stephen L.
supporting information; experimental part, p. 2721 - 2724 (2009/05/27)
(Chemical Equation Presented) A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.
