Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System

Abstract

Abstract:The direct sulfonamidation of primary and secondary benzylic alcohols catalyzed by a 2,3,4,5-tetrafluorophenylboronic acid/oxalic acid co-catalytic system was examined. The reaction proceeds under mild conditions with readily available

Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation

“…Although the use of pentafluorophenylboronic acid 3 in combination with oxalic acid 8 has been reported for dehydrative Friedel-Crafts reactions, [13,16] the exact nature of the intermediate catalytic species has not previously been studied. A preparative experiment reacting pentafluorophenylboronic acid 3 with oxalic acid 8 (2 equiv.)…”

“…The same catalytic system has also been applied to the transposition of allylic alcohols [15] and the intermolecular alkylation of sulfonamide nucleophiles using benzylic alcohols. [16,17] To date, arylboronic acid-catalysed intermolecular…”

Copper-catalyzed synthesis of diarylamines using p-toluene sulfonamides and benzhydrol derivatives under homogeneous borrowing hydrogen conditions

“…Alongside all advances in rhodium catalyst addition of the organometallic reagents to imines producing diarylamine [12], numerous methods were reported in the literature, based on hydrogenation of imines and enamines [13,14], amination of ketones and amination of alkyl halides [15] (Scheme 1). Amongst them, hydrogenation reactions are much more important in research or industry, and the use of either hydrogen gas or transfer hydrogenation reduction with Brønsted [16] or Lewis catalysts [17][18][19] and transition metal complexes of Ir, Pd, Rh is well established [20][21][22]. Notwithstanding many reports on these reactions, these multistep pathways often suffer from the instability of the intermediates, low atom economy and the production of byproducts.…”

Straightforward and Sustainable Synthesis of Sulfonamides in Water under Mild Conditions

“…Another synthetic pathway is the functionalization of sulfonamides. This can be achieved by using a wide variety of reactants such as aryl nonaflates, aryl halides, alcohols, aldehydes or boronic acids . In addition, all the methods described in the literature use organic solvents such as dichloromethane and/or toxic activating agents such as thionyl chloride for the preparation of the sulfonamides.…”