Cp₂TiCl/D₂O/Mn, a formidable reagent for the deuteration of organic compounds

Abstract

SummaryCp2TiCl/D2O/Mn is an efficient combination, sustainable and cheap reagent that mediates the D-atom transfer from D2O to different functional groups and can contribute to the synthesis of new deuterated organic compounds under friendly experimental conditions and with great economic advantages.

The Proven Versatility of Cp2TiCl

“…Cp 2 TiCl finds another interesting application in the deuteration of organic compounds and the synthesis of β-deuterated alcohols for their use as internal standards in food analysis . Cp 2 TiCl/D 2 O/Mn is an inexpensive, efficient, and sustainable combination that mediates the deuterium-atom transfer from D 2 O to the functional targets of this SET reagent (epoxides, ,, ozonides, ketones, activated halides, , alkynes, and alkenes) and, therefore, contributes to the synthesis of deuterated organic compounds under green experimental conditions and with great economic advantages.…”

“…The presence of an allylic acetate (241, 247) (Scheme 29) or an aromatic ring (238, 244, 252) prepares the system for the completion of the carbon skeleton, thus allowing the synthesis of umbrosone (240), 67 the marine furanoditerpenoid 243, 68 aureol (246), 69 eurifuran (250), 70 cyclozonarone (251), 71 ambrox (249), 72 or pupehedione (254). 73 Cp 2 TiCl finds another interesting application in the deuteration of organic compounds 74 and the synthesis of β-deuterated alcohols for their use as internal standards in food analysis. 75 Cp 2 TiCl/D 2 O/Mn is an inexpensive, efficient, and sustainable combination that mediates the deuterium-atom transfer from D 2 O to the functional targets of this SET reagent (epoxides, 7,32,75 ozonides, 26 ketones, 29b activated halides, 33c,d alkynes, and alkenes 53 ) and, therefore, contributes to the synthesis of deuterated organic compounds under green experimental conditions and with great economic advantages.…”

Preparation of Deuterium Labeled Compounds by Pd/C-Al-D2O Facilitated Selective H-D Exchange Reactions

“…Due to the significance of deuterated organic compounds, the development of efficient and selective deuteration methods attracted great interests [ 13 , 14 ]. Various combinations of deuterium source and reagents/catalysts are available to carry out deuteration reactions including acid-base catalyzed reactions [ 15 ], deuterated reagents-based methods (such as LiAlD 4 [ 16 ]) and transition metal-catalyzed approaches [ 17 , 18 , 19 ]. Most methods, however, do not conform to the recent expectations and standards of sustainable synthesis.…”

Base-Mediated Deuteration of Organic Molecules: A Mechanistic Insight

“…They have also utilized the similar protocol for the deuteration of terminal alkyne (Scheme f). In 2016, Rosales and Rodríguez-García have reported an elegant approach for the deuteration of organic compounds in the presence of Cp 2 TiCl/D 2 O/Mn . To the best of our knowledge, the phenomena of deuteration have not been applied to the organic reactions such as nucleophilic addition reaction and domino processes.…”

“…In 2016, Rosales and Rodri ́guez-Garci ́a have reported an elegant approach for the deuteration of organic compounds in the presence of Cp 2 TiCl/D 2 O/Mn. 15 To the best of our knowledge, the phenomena of deuteration have not been applied to the organic reactions such as nucleophilic addition reaction and domino processes. As an extension of our current research on superbasic chemistry, 16 we endeavor to propose our new finding of N-,S-,O-nucleophilic deuterioaddition reaction with alkynes using DMSO-d 6 as a deuterium source (Scheme 1g).…”