The synthesis and evaluation of structural analogues and isosteres are of central importance in medicinal and agricultural chemistry. The sulfonamide functional group represents one of the most important amide isosteres in contemporary drug design, and about 500 such compounds have overcome both the pharmacological and regulatory hurdles that precede studies in humans. The mono aza analogues of sulfonamides, that is, sulfonimidamides, are rapidly gaining popularity as a novel functional group among synthetic chemists involved in the design of biologically active compounds for both pharmaceutical and agrochemical applications. Herein, we review these recent developments to showcase the promise of this functional group.

Sulfonyl fluoride (SF) containing substances are currently attracting enormous attention among practitioners of both chemical biology and synthetic organic chemistry. The groups of Jones and Liskamp have demonstrated the potential of sulfonyl fluorides as selective covalent inhibitors in studies related to drug discovery and chemical biology, respectively, in the last few years. The Sharpless group has extended the repertoire of “click‐reactions” to those involving sulfonyl fluorides, that is, sulfur–fluoride exchange (SuFEx), a development that quickly triggered the interest in this functional group in the community of synthetic organic chemists. In this microreview, we aim to give an account of the synthetic chemistry surrounding sulfonyl fluoride containing substances from a historical perspective to present day developments.

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Herein, we report an efficient, ligand-free, and additive-free Suzuki-Miyaura coupling that is compatible with the aromatic sulfonyl fluoride functional group. The protocol proceeds at room temperature, on water, and offers facile access to a wide range of biaryl sulfonyl fluorides as bioorthogonal "click" reagents.

Herein, we report an operationally simple, ligand- and additive-free oxidative boron-Heck coupling that is compatible with the ethenesulfonyl fluoride functional group. The protocol proceeds at room temperature with chemoselectivity and E-isomer selectivity and offers facile access to a wide range of β-aryl/heteroaryl ethenesulfonyl fluorides from commercial boronic acids. Furthermore, we demonstrate a "one-pot click" reaction to directly transform the products to aryl-substituted β-sultams.