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Abstract The first C−SCF3/SeCF3cross‐coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3or Me4NSeCF3, and organohalides as substrates are reported. The new methodology enables a one‐stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio‐ and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late‐stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio‐ and selenoethers for pharmaceutical and agrochemical research and development.
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Abstract A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C−C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one‐pot synthesis of ketones from primary alcohols and α‐ketoamides from aldehydes.more » « less
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Abstract A novel, air and thermally stable, yet highly reactive trifluoromethylthiolating reagent, CF 3 SO 2 SCF 3 ( 1 ), was prepared easily in one step from commercially inexpensive CF 3 SO 2 Na and Tf 2 O. 1 is a highly versatile and atom‐efficient reagent that can generate one equivalent of CF 3 S + , two equivalents of CF 3 S − , or a combination of CF 3 S⋅/CF 3 ⋅ species. Many high‐yielding CF 3 S reactions of C , O , S , and N ‐nucleophiles were achieved, including the simple‐step preparations of many reported CF 3 S reagents. 1 delivered a hitherto hard‐to‐synthesize ArOSCF 3 that was followed by a novel CF 3 S II ‐rearrangement. Through Cu or TDAE/Ph 3 P combinations, 1 generated two equivalents of CF 3 S anion species, and the photo‐catalyzed reactions of alkenes with 1 provided CF 3 /CF 3 S‐containing products in high atom‐efficiency.more » « less
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We have developed a versatile transition metal-free cross-coupling reaction between fluorinated benzyl electrophiles and alkenylboronic acids in the presence of the equivalent amount of alkali metal salts such as K 3 PO 4 . This transition metal-free protocol gives good chemical yields for a wide range of substrates and demonstrates good functional group tolerance.more » « less
