Sachin Bhausaheb Wagh

Fluorescent probes have gained profound use in biotechnology, drug discovery, medical diagnostics, molecular and cell biology. The development of methods for the translation of fluorophores into fluorescent probes continues to be a robust field for medicinal chemists and chemical biologists, alike. Access to new experimental designs has enabled molecular diversification and led to the identification of new approaches to probe discovery. This review provides a synopsis of the recent lessons in modern fluorescent probe discovery.

A pocket-templated Paal–Knorr reaction delivers fluorescent COX-2 probes.

This work reports gold-catalyzed oxidative alkenylations of quinoline N-oxides with propargyl aryl thioethers to afford 3-hydroxy-1-alkylidenephenylthiopropan-2-one via a 1,3-sulfur group migration. The mechanism of this reaction is postulated to involve an α-oxo gold carbene intermediate followed by formation of a four-membered sulfonium ring that is ring-opened by one H₂O to form a gold enolate. A final condensation of this enolate with a second quinoline N-oxide delivers an alkenylation product accompanied by a 1,3-sulfur shift.

This work reports gold-catalyzed oxidative cycloalkenations of phenyl propargyl ethers and phenoxyalkynes with quinoline N-oxides to afford 4-alkylidenechroman-2-ones and 3-alkylidenebenzofuran-2-ones, respectively. This catalytic sequence involves one alkyne, one aryl nucleophile and two discrete quinoline oxides. We postulate a mechanism involving an initial formation of an α-oxo gold carbene that is attacked by a tethered arene to form a gold enolate, further reacting with a second quinoline N-oxide to complete the olefination process.

The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile‐directed chemoselectivity through cooperative catalysis. For 1‐alkyn‐4‐ols and 2‐ethynylphenols, their gold‐catalyzed nitrone oxidations afforded N‐containing dihydrofuran‐3(2H)‐ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O‐H‐N hydrogen‐bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3‐alkylidenebenzofuran‐2‐ones, as controlled by a C‐H‐O hydrogen‐bonding motif.

Gold-catalyzed synthesis of buta-1,3-dien-2-yl esters by the reaction of propargyl esters with vinylazides is described; the reaction mechanism is postulated to involve a vinyl attack of vinylazides at alkenyl gold carbenes.