A chemoselective deoxygenation of N-oxides by sodium borohydride–Raney nickel in water

Ultrasonic Preparation of Porous Silica-Dye Microspheres: Sensors for Quantification of Urinary Trimethylamine N-Oxide

“…The general steps of this process involve (1) removal of volatile amines (e.g., ammonia, dimethylamine, and TMA) from the simulated urine, (2) pretreatment of the solution TMAO using a reductant and catalyst, and (3) a sampling protocol for subsequently produced TMA. Specifically, an enzyme-free reagent (Raney Ni/NaBH 4 ) has been found to be an effective system for the highly selective deoxygenation of N -oxides in the aqueous phase, which permits the conversion of TMAO to TMA with a high yield (>95%) even at room temperature (Scheme ) and in the presence of carbonyls (including urea, uric acid, creatine, or creatinine) …”

Preparation of Pyridine N-oxide Derivatives in Microreactor

“…All other analytical data of 2c are identical to the ones described in the literature. [47] 2-Benzylpyridine N-oxide 131 μl 1d (135.38 mg, 0.8 mmol) is stirred in 0.5 ml acetic acid at 70°C and 641 µl (705.6 mg, 5.6 mmol) 27% water solution of H 2 O 2 is added. The reaction is stirred at 30 min and checked by HPLC (262 nm, RT: 1d: 3.6, 2d: 4.8).…”

B(C6F5)3‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

“…[2] In addition, the reduction of sulfoxides and amine N-oxides into their corresponding sulfides and amines is an important reaction owing to its considerable utility in organic synthesis. [13] On the other hand, reagents used in the deoxygenation of amine Noxides include In, [14] Mo(CO) 6 , [15] Cu, [16] NbCl 5 /Zn, [17] Raney nickel, [18] diboron reagents, [19] and gold nanoparticles. [13] On the other hand, reagents used in the deoxygenation of amine Noxides include In, [14] Mo(CO) 6 , [15] Cu, [16] NbCl 5 /Zn, [17] Raney nickel, [18] diboron reagents, [19] and gold nanoparticles.…”

“…[5] The past decade has witnessed spectacular advances in metal-free catalytic reductions, particularly with the use of B(C 6 F 5 ) 3 /silanes. [13] On the other hand, reagents used in the deoxygenation of amine Noxides include In, [14] Mo(CO) 6 , [15] Cu, [16] NbCl 5 /Zn, [17] Raney nickel, [18] diboron reagents, [19] and gold nanoparticles. Over the past years, many systems have been employed for the deoxygenation of sulfoxides, including reagents such as silane/MoO 2 Cl 2 , [6] oxo complexes, [7] gold nanoparticles, [8] zinc(II) trifluoromethanesulfonate/bis(pinacolato)diboron [Zn(OTf ) 2 /B 2 (pin) 2 ] or Zn(OTf ) 2 /boranes, [9] SOCl 2 , [10] Fe powder, [11] ruthenium nanoparticles, [12] and I 2 .…”

“…Over the past years, many systems have been employed for the deoxygenation of sulfoxides, including reagents such as silane/MoO 2 Cl 2 , [6] oxo complexes, [7] gold nanoparticles, [8] zinc(II) trifluoromethanesulfonate/bis(pinacolato)diboron [Zn(OTf ) 2 /B 2 (pin) 2 ] or Zn(OTf ) 2 /boranes, [9] SOCl 2 , [10] Fe powder, [11] ruthenium nanoparticles, [12] and I 2 . [13] On the other hand, reagents used in the deoxygenation of amine Noxides include In, [14] Mo(CO) 6 , [15] Cu, [16] NbCl 5 /Zn, [17] Raney nickel, [18] diboron reagents, [19] and gold nanoparticles. [20] However, many of the reagents employed for these deoxygenation processes are expensive, [6,8,12] sensitive to both air and moisture, [15,17] or involve the use of transition metals under harsh conditions.…”