An efficient and practical cascade oxidation/halogenoaminocyclization of trifluoromethylated homoallylic N-acylhydrazines is developed. The protocol enables an efficient access to various biologically interesting CF-containing pyrazoline compounds from readily accessible trifluoromethylated homoallylic N-acylhydrazines in good to excellent yields under mild conditions without any other additives or catalysts. The produced pyrazoline compounds can be further manipulated to other more complicated derivatives through transformation of residual halogen atom.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.7b02934 | DOI Listing |
Chem Commun (Camb)
September 2024
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. China.
A photocatalytic trifluoromethylation/cyclization reaction of -allyl and -homoallyl aldehyde hydrazones with trifluoromethyl thianthrenium triflate was developed for the synthesis of trifluoromethylated dihydropyrazoles and tetrahydropyridazines. Besides, PhI(OCCHF) was employed to realize the construction of difluoromethylated dihydropyrazoles and tetrahydropyridazines. These protocols exhibit a broad substrate scope and good functional group tolerance.
View Article and Find Full Text PDFNat Chem
December 2022
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, USA.
Molecules that contain one or more fluorine atoms are crucial to drug discovery. There are protocols available for the selective synthesis of different organofluorine compounds, including those with a fluoro-substituted or a trifluoromethyl-substituted stereogenic carbon centre. However, approaches for synthesizing compounds with a trifluoromethyl- and fluoro-substituent stereogenic carbon centre are far less common.
View Article and Find Full Text PDFOrg Lett
July 2022
Chemical Synthesis and Pollution Control Key Laboratory of Si-chuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China.
The intermolecular addition of allylic copper species generated from diene and copper hydride remains elusive. Herein copper hydride catalyzed asymmetric cross reductive coupling of conjugated dienes and ketoimines including trifluoromethyl ketoimines and α-iminoacetates was first achieved using chiral Ph-BPE as the ligand, providing rapid access to structurally and optically enriched homoallylic amines containing two vicinal stereogenic centers with up to 95% yield, 99% ee, and 11:1 diastereoselectivities.
View Article and Find Full Text PDFOrg Lett
April 2022
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang 37673, Republic of Korea.
We report the transition-metal-free defluorinative C-C bond-forming reaction of trifluoromethyl alkenes with -(diborylalkyl)lithiums. This synthetic strategy provides access to a variety of 4,4-difluoro homoallylic diboronate esters, which serve as versatile intermediates in the efficient preparation of valuable -difluoroalkene derivatives. Further synthetic modifications are conducted to demonstrate the synthetic utility of the obtained 4,4-difluoro homoallylic diboronate esters.
View Article and Find Full Text PDFJ Am Chem Soc
December 2020
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
Chiral α-substituted allylboronic acids were synthesized by asymmetric homologation of alkenylboronic acids using CF/TMS-diazomethanes in the presence of BINOL catalyst and ethanol. The chiral α-substituted allylboronic acids were reacted with aldehydes or oxidized to alcohols in situ with a high degree of chirality transfer. The oxygen-sensitive allylboronic acids can be purified via their isolated diaminonaphthalene (DanH)-protected derivatives.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!