The nickel-catalyzed reduction of secondary and tertiary amides to give amine products is reported. The transformation is tolerant of extensive variation with respect to the amide substrate, proceeds in the presence of esters and epimerizable stereocenters, and can be used to achieve the reduction of lactams. Moreover, this methodology provides a simple tactic for accessing medicinally relevant α-deuterated amines.
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http://dx.doi.org/10.1021/acs.orglett.7b00683 | DOI Listing |
Org Lett
December 2024
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, People's Republic of China.
Metal-catalytic conversion of polysulfide reagents is a major challenge in organic synthesis due to its challenging activation modes of multiple S-S bonds. The utilization of aryl di- and trithiosulfonates in nickel-catalyzed reductive coupling with aryl halides has been unexplored. Herein, we unprecedentedly describe PPh and Zn-collaborative reduction-induced nickel-catalytic selective C-S coupling of aryl di/trithiosulfonates with aryl halides to access sulfides over common disulfides or trisulfides.
View Article and Find Full Text PDFACS Med Chem Lett
October 2024
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry and School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China.
Synthesizing FimH antagonists is challenging because of their densely functionalized and stereochemically complex -mannoside structures, resulting in low yields and lengthy processes. We present an efficient method for synthesizing -mannoside FimH antagonists by nickel-catalyzed reductive coupling and stereocontrolled reduction, thereby significantly simplifying the process and enabling the synthesis of FimH antagonists in just four steps with an overall yield of 34-50%. This efficient synthesis holds significant potential for the rapid development of analogues targeting the treatment of urinary tract infections or Crohn's disease caused by ().
View Article and Find Full Text PDFJ Am Chem Soc
October 2024
Department of Chemistry, National University of Singapore, 4 Science Drive 2, Singapore 117544, Republic of Singapore.
ACS Catal
July 2024
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Fluoroalkyl fragments have played a critical role in the design of pharmaceutical and agrochemical molecules in recent years due to the enhanced biological properties of fluorinated molecules compared to their non-fluorinated analogues. Despite the potential advantages conferred by incorporating a difluoromethyl group in organic compounds, industrial adoption of difluoromethylation methods lags behind fluorination and trifluoromethylation. This is due in part to challenges in applying common difluoromethyl sources towards industrial applications.
View Article and Find Full Text PDFChemistry
December 2024
Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay, 91400, Orsay, France.
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