76043-69-1Relevant academic research and scientific papers
Chromium-carbyne complexes: Intermediates for organic synthesis
Bejot, Romain,He, Anyu,Falck, John R.,Mioskowski, Charles
, p. 1719 - 1722 (2007)
(Chemical Equation Presented) On the same route: Chromium-carbyne complexes are readily prepared by treatment of 1,1,1-trichloromethyl reagents with chromium(II) chloride. They serve as intermediates in the selective formation of a wide variety of products, such as alkynes, alkenes, β-hydroxy ketones, aldehydes, allylic alcohols, and allenes (see scheme, E = electrophile).
Enantioselective Addition of Alkynes to α,α-Dichlorinated Aldehydes
Sempere Molina, Yeshua,Ruchti, Jonathan,Carreira, Erick M.
, p. 743 - 745 (2017)
Enantioselective addition of terminal alkynes to α,α-dichlorinated aldehydes employing Zn(OTf)2/NME is disclosed. The propargylic alcohols obtained are accessed in good yields and high enantioselectivity from easily accessible α,α-dichloroaldeh
An Efficient Route to Aliphatic 2,2-Dichloroaldehydes via Chlorination of Aldehydes or Alcohols with the System Cl2/Quaternary Ammonium Chloride
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco,Pagnoni, Ugo M.,Parsons, Andrew F.,Pinetti, Adriano
, p. 2173 - 2178 (2003)
An effective and low waste method for preparing aliphatic 2,2-dichloroaldehydes has been achieved by halogenation of aldehydes or alcohols with Cl2, using tetraalkylammonium chlorides as recoverable catalysts.
2,2-Dichlorination of aldehydes with the 2,6-lutidine·HCl/Cl2/CH2Cl2 system: An environmentally benign process suitable for scale up
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco,Libertini, Emanuela,Pagnoni, Ugo Maria,Roncaglia, Fabrizio
, p. 7507 - 7511 (2000)
An effective and environmentally benign preparation of 2,2-dichloroaldehydes has been achieved by chlorination of aldehydes with Cl2(g) in CH2Cl2, using 2,6-lutidine hydrochloride as recoverable catalyst. Remarkable qualif
Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes
Hutchinson, George,Alamillo-Ferrer, Carla,Burés, Jordi
supporting information, p. 6805 - 6809 (2021/05/29)
The enantioselective aminocatalytic α-chlorination of aldehydes is a challenging reaction because of its tendency to proceed through neutral intermediates in unselective pathways. Herein we report the rational shift to a highly selective reaction pathway involving charged intermediates using hexafluoroisopropanol as solvent. This change in mechanism has enabled us to match and improve upon the yields and enantioselectivities displayed by previous methods while using cheaper aminocatalysts and chlorinating agents, 80-95% less amount of catalyst, convenient temperatures, and shorter reaction times.
Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles
Davidson, Robert W. M.,Fuchter, Matthew J.
, p. 11638 - 11641 (2016/10/04)
The N-heterocyclic carbene (NHC)-catalysed redox amidation reaction is poorly developed and usually requires catalytic co-additives for electron-rich amine nucleophiles. We report a masking strategy (using CO2) that couples release of the free amine nucleophile to catalytic turnover, and in doing so, enables direct catalytic redox amidation of electron-rich amines.
Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes
Jimeno, Ciril,Cao, Lidong,Renaud, Philippe
, p. 1251 - 1255 (2016/02/19)
Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.
2,2-dichloroaldehydes and 2,2-dichlorocarboxylic acids from 2- picoline·HCl catalyzed chlorination of aldehydes
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco
, p. 146 - 148 (2007/10/03)
An efficient preparation of 2,2-dichloroaldehydes and 2,2- dichlorocarboxylic acids has been achieved by chlorination of aldehydes using 2-picoline hydrochloride as recoverable catalyst.
2,2-DICHLOROALDEHYDES FROM ALDEHYDES AND ALCOHOLS BY CHLORINATION IN DIMETHYLFORMAMIDE
Buyck, L. De,Verhe, R.,Kimpe, N. De,Courtheyn, D.,Schamp, N.
, p. 441 - 458 (2007/10/02)
A method is described for the synthesis of α,α-dichloroaldehydes, free from monochloroaldehyde, by chlorination of aldehydes or alcohols in dimethylformamide at 40-90 deg C.Results are reported for : (yield percent) propanal (90), butanal (78), pentanal (78), 3-methylbutanal (90), propanol (64), butanol (78), 3-methylbutanol (52), pentanol (66), 3,3-dimethylbutanol (86), hexanol (66), 2-phenylethanol (51), 3-phenylpropanol (54), 1,5-pentanediol , 1,6-hexanediol .Oxidative conversion (KMnO4, K2Cr2O7, H2O2-NaHCO3) into α,α-dichlorocarboxylic acids and methyl esters is discussed.
