1,2‐Bis(trifluoromethylthiolation) of Aromatic Epoxides with AgSCF₃

Abstract

A tandem ring‐opening and deoxytrifluoromethylthiolation of aromatic epoxides with AgSCF3 and nBu4NI/KI has been developed. This protocol provides a convenient access to a series of novel 1,2‐bis(trifluoromethylthiolated) products, which has been rarely reported and might find applications in medicinal and material chemistry.

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

“…Only trace of mono(trifluoromethylthiolated) product was detected, and most of the substrate 1a was not converted. To the best of our knowledge, the combination of bis(trifluoromethylthiolation) [36,[39][40][41] and cascade cycli- With the optimized reaction conditions in hand, we then set out to explore the substrate scope of N-[(3-aryl)propioloyl]indoles (Scheme 2). First, we explored the effect of the substitution on the indole ring.…”

Enzymatic Kinetic Resolution by Addition of Oxygen

“…The flavin-dependent Baeyer-Villiger monooxygenase (BVMO) catalyses the oxidation of both cyclic and acyclic ketones to lactones and esters, respectively. [18] Traditional chemical methods to achieve the Baeyer-Villiger (BV) transformation [19] typically employ stoichiometric oxidants containing the peroxy linkage; such reagents are often heat-and shock-sensitive, toxic, and expensive, all of which severely constrain their large-scale industrial application. [20] BVMOs harness aerial molecular oxygen to produce the reactive oxidant in situ at low concentration, offering a safer, green alternative with considerable effort now being made to expand the traditionally limited substrate scope of these enzymes and to improve selectivity.…”

Deoxygenative 1,1‐Bis‐trifluoromethylthiolation of Aromatic Aldehydes to Access Bis(trifluoromethylthio)methylarenes

“…The groups of Tlili&Billard [9a] and Daugulis [9b] reported 1,2‐bis‐trifluoromethylthiolation of alkynes and arynes, respectively. Our group also developed 1,2‐bis‐trifluoromethylthiolation of propiolic acid derivatives, [10a] buta‐2,3‐dienoic acids, [10b] and aromatic epoxides [10c] . In the cases of 1,1‐bis‐trifluoromethylthiolation reactions, only two examples have been reported.…”