Sulfonimidamide as a directing agent for Pd-catalyzed regioselective oxidative C–H acyloxylation of arenes

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

“…Bakthadoss et al reported the first ortho-CÀ H activation process using a palladium catalyst to introduce hydroxy and acetoxy functionalities (113 and 114) onto unactivated aryl sp 2 carbons of oxobenzoxazine derivatives (112) (Scheme 38). [118] It's interesting how easily and quickly this intermolecular CÀ H functionalization event occurred with excellent chemo-and site selectivity.…”

“…Diazo compound multicomponent reactions have received a lot of interest recently. In this work, a three-component intermolecular acetoxyaminoalkylation (119) of tertiary aryl amines (118) and PIDA with α-diazo amides (117) was described by Studer et al (Scheme 40). [120] The optimized reaction parameters are: α-diazo amide (0.1 mmol), N,N-dimethylaniline (0.3 mmol) and PIDA (0.2 mmol) in methanol at RT in air.…”

Sulfonimidamide as Directing Group for Pd‐mediated ortho‐C−H Chlorination of Arenes

“…For the past few years, our group is involved in developing novel methods for synthesizing various N ‐functionalized SIAs [19–23] . As a part of our research work with SIA, we have introduced SIA as directing group (DG) for ortho ‐acetoxylation of arenes (Scheme 1b ) [24] . In order to extend the synthetic scope of SIA as DG, herein, we have incorporated chlorine at the ortho position of arene of N ‐aroyl SIA.…”

“…[19][20][21][22][23] As a part of our research work with SIA, we have introduced SIA as directing group (DG) for ortho-acetoxylation of arenes (Scheme 1b). [24] In order to extend the synthetic scope of SIA as DG, herein, we have incorporated chlorine at the ortho position of arene of N-aroyl SIA. The reaction of N-aroyl SIA with N-chlorosuccinimide (NCS) in the presence of Pd-catalyst provided the corresponding ortho-chlorinated products in good yields (Scheme 1c).…”

One-Pot Tandem Oxidative Bromination and Amination of Sulfenamide for the Synthesis of Sulfinamidines

“…In the past few years, the synthesis of sulfur derivatives has received great attention from academic research groups and pharmaceutical companies alike . Sulfone, sulfonamide, and sulfonic ester are well-established S­(VI) functionalities that feature in most sulfur-containing FDA-approved drugs, and recently, their aza analogues such as sulfoximine, ,, sulfonimidamide, and sulfonimidate ester have been growing interest in the development of synthetic methodologies . Replacement of one of the oxygen atoms with nitrogen provides favorable stability and solubility, multiple hydrogen-bond acceptor/donor functionalities, and structural diversity. , However, sulfinamidines, the monoaza analogues of sulfinamides, received limited attention from both organic chemists and pharmaceutical chemists.…”