Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

NCBSI/KI: A Reagent System for Iodination of Aromatics through In Situ Generation of I-Cl

“…29 Similarly, in situ I-Cl generation followed by iodination were reported using NCS/ NaI-trifluoroacetic anhydride 30 and NCS/KI−HI system. 31 The NCS activation correlates the need for protonation of the carbonyl group to increase the bond length from 1.707 to1.825 Å and generate the electrophile reported by Prakash et al 21 After working on chlorination of aromatics and oxidation of alcohols using NCBSI reagent, 32,33 our research group has developed an iodinating system of NCBSI/KI, which generates I-Cl in situ without activation. We were keen on applying this protocol for the iodination of activated arenes.…”

“…After working on chlorination of aromatics and oxidation of alcohols using NCBSI reagent, , our research group has developed an iodinating system of NCBSI/KI, which generates I-Cl in situ without activation. We were keen on applying this protocol for the iodination of activated arenes.…”

“…We were keen on applying this protocol for the iodination of activated arenes. Our previous research on NCBSI reagent revealed high electrophilicity due to a longer bond length (1.848 Å), lower BDE (40.36 kcal mol –1 ), and higher absolute charge density on nitrogen (−0.658) compared to other N -chloro reagents. , Therefore, we investigated the formation of I-Cl by reaction of various N -chloro reagents with potassium iodide in anhydrous acetonitrile over 12 h (Table ).…”

Manipulating Activity and Chemoselectivity of a Benzaldehyde Lyase for Efficient Synthesis of α-Hydroxymethyl Ketones and One-Pot Enantio-Complementary Conversion to 1,2-Diols

“…21−23 Owing to its great importance, the development of efficient methods for the synthesis of α-hydroxymethyl ketones is an important research focus in the pharmaceutical industry. The chemical methods for the preparation of α-hydroxymethyl ketones involve iodinepromoted activation, oxidation, and dioxygenation of alkenes, 24,25 substitution of α-haloketones, 26,27 oxidation of diols, 28 decarboxylative oxidation of carboxylic acids, 29,30 and hydroxymethylation of aldehydes by N-heterocyclic carbenes (NHCs). 4,31 Compared to conventional chemical methods that often require high toxic and cost reagents, harsh reaction conditions, and sometimes low isolated yields, biocatalysis has become an attractive approach to prepare α-hydroxymethyl ketones.…”

Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents

“…Inspired by reports that employ saccharin anions as O-centered nucleophilic source [43,44], here, we evaluate the possibility of employing N-iodosaccharins as novel bifunctional oxyiodination reagents. Based on our previous works [45][46][47][48][49][50][51][52] on the development of sustainable transformations, we now report on the intermolecular oxyiodination and oxychlorination of alkynes that employ N-iodosaccharin or N-chlorobenzenesulfonimide (NCBSI) [53][54][55] as bifunctional reagents (Scheme 1D). Scheme 1.…”