In this study, the successful titanium tetrachloride-catalyzed reduction of aldehydes, ketones, carboxylic acids, and nitriles with borane-ammonia was extended to the reduction (deoxygenation) of a variety of aromatic and aliphatic pri-, sec- and tert-carboxamides, by changing the stoichiometry of the catalyst and reductant. The corresponding amines were isolated in good to excellent yields, following a simple acid-base workup.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10301125 | PMC |
http://dx.doi.org/10.3390/molecules28124575 | DOI Listing |
Molecules
June 2023
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA.
In this study, the successful titanium tetrachloride-catalyzed reduction of aldehydes, ketones, carboxylic acids, and nitriles with borane-ammonia was extended to the reduction (deoxygenation) of a variety of aromatic and aliphatic pri-, sec- and tert-carboxamides, by changing the stoichiometry of the catalyst and reductant. The corresponding amines were isolated in good to excellent yields, following a simple acid-base workup.
View Article and Find Full Text PDFChemistry
March 2020
Department of Chemistry and Biochemistry, University of Texas at El Paso, El Paso, TX, 79968, USA.
Two electron-reduction of the Ti guanidinate complex (Im N)( guan)TiCl gives (η -Im N)( guan)Ti (1 ) and (Im N)( guan)Ti(η -C H ) (1 ) ( guan=[(tBuC=N)C(NXylyl) ] , Xylyl=2,5-dimethylphenyl) in the absence or presence of benzene, respectively. These complexes have been found to hydrogenate monocyclic and polycyclic arenes under relatively mild conditions (150 psi, 80 °C)-the first example of catalytic, homogeneous arene hydrogenation with TON >1 by a Group IV system.
View Article and Find Full Text PDFJ Org Chem
March 2019
School of Chemistry, Center for Synthesis and Chemical Biology , University College Dublin, Dublin D04 N2E5 , Ireland.
Reduction of a range of benzo-fused cyclic sulfonamides has been accomplished using low-valent titanium. This operationally simple method generates the corresponding aryl-substituted cyclic amines, typically, with good conversion. Notably, unlike our previous Li-NH-based method, loss of heteroatom-based substituents (X) on the aromatic ring does not readily occur, and the robustness of this method was demonstrated with a synthesis of the Sceletium alkaloid mesembrane.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2016
Department of Chemistry, University of Texas at El Paso, El Paso, TX, 79968, USA.
Two-electron reduction of the Ti compound ( guan)(Im N)Ti(OTf) (3) gives the arene-masked complex ( guan)(η -Im N)Ti (1) in excellent yield. Upon standing in solution, 1 converts to a Ti metallacycle (4) through dehydrogenation of a pendant isopropyl group. Spectroscopic evidence shows this transformation initially proceeds via the oxidative addition of a C(sp )-H bond and can be reversed upon exposure of 4 to H .
View Article and Find Full Text PDFSteroids
October 2014
Department of Applied Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea. Electronic address:
An efficient method for the synthesis of aryl aminocholestanes, using a chlorotriisopropoxytitanium(IV)-mediated reductive amination reaction of 5α-cholestane-3,7-dione, is reported. A series of 3,7-diarylaminocholestane derivatives were prepared according to this methodology in up to 98% yield. These compounds were primarily characterized by (1)H NMR, (13)C NMR, and mass spectrometry.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!