(Bu₃Sn)₂–TBAF: a new combination reagent for the reduction and deuteration of aryl bromides and iodides

Abstract

The combination of (Bu(3)Sn)(2) and TBAF has been shown to reduce aromatic bromides and iodides in excellent yields under mild conditions. When the residual water in TBAF is exchanged for D(2)O, the halogen is replaced by a deuterium atom.

KF–Silica as a stationary phase for the chromatographic removal of tin residues from organic compounds

“…Using the hydrodehalogenation of aryl halide 1 with the tributyltin hydride-TBAF reagent combination as a representative procedure (Scheme 1), 18 chromatographic purification of the concentrated product mixture using silica alone gave 2 contaminated with ca. 50 mol% of organotin impurities (as evidenced by characteristic signals for the butyl residues between d H 1.8 and 0.9 ppm in the 1 H NMR spectrum, Fig.…”

Potassium carbonate–silica: a highly effective stationary phase for the chromatographic removal of organotin impurities

“…Scheme 1 Applications of the method in halide reduction, Stille coupling, Bu 3 SnH-mediated radical cyclisation and hydrostannylation reactions. [9][10][11][12][13]…”

“…We have applied the method in Bu 3 SnH-mediated reductions of aryl halides and acid chlorides, 9,10 Stille coupling 11 and tin-mediated radical cyclisation reactions (Scheme 1). 12,13 In each case, 1 H NMR analysis of the purified products showed them to be free of organotin impurities (see ESIz), including situations in which a low-yielding product had to be separated from a complex product mixture containing substantial organotin residues.…”

Coupling photocatalytic overall water splitting with hydrogenation of organic molecules: a strategy for using water as a hydrogen source and an electron donor to enable hydrogenation

“…37–44 As a result, much attention has been devoted to the deuteration of aromatic rings. 37–44 One of the most effective strategies is the deuteration of aryl halides using DMSO-D 6 , 45 CD 3 OD, 46 DCOONa, 47 THF-d 8 , 48 CH 3 OD 49 and D 2 O 50–54 as deuterium sources (Scheme 1b), among which D 2 O is undoubtedly the most attractive deuteration reagent from the perspective of safety, cost and handling. However, those methods for the deuteration of aryl halides with D 2 O suffer from an expense of polluting reductants such as sodium formate, triethanolamine, sodium sulfite and (Bu 3 Sn) 2 .…”

“…However, those methods for the deuteration of aryl halides with D 2 O suffer from an expense of polluting reductants such as sodium formate, triethanolamine, sodium sulfite and (Bu 3 Sn) 2 . [50][51][52][53][54] Thus we applied our strategy to the deuteration of aryl halides with D 2 O to avoid using those pollutive reductants, which provides an effective and controllable method for synthesizing high value-added deuterated aromatic compounds (Scheme 1c), and the results are reported herein.…”