A novel and efficient palladium-catalysed direct di-heteroarylation of 1,2-dichloroperfluorocyclopentene with a variety of heteroarenes is reported, giving rise to 1,2-di(heteroaryl)ylperfluorocyclopentene photochromic compounds. The reaction proceeds with thiazoles, thiophenes or furan derivatives and tolerates various substituents.
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http://dx.doi.org/10.1039/c2cc37046h | DOI Listing |
Chem Commun (Camb)
October 2023
School of Pharmacy, Jiangsu University, Zhenjiang 212013, P. R. China.
The direct carbonylation of readily available nitro compounds is more attractive and straightforward than the use of traditional amines as nucleophiles. Herein, a practical palladium-catalysed double carbonylation of nitroarenes with -dihaloarenes has been developed for the construction of various -aryl phthalimides. Key to the success of this transformation is the use of Mo(CO), which acts as both a reducing agent and a solid carbonyl source.
View Article and Find Full Text PDFChem Commun (Camb)
July 2023
Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
We report herein the palladium-catalysed mono-selective C-H arylation of [2.2]paracyclophane (PCP) with diverse aryl iodides in the absence of any pendant directing groups, providing straightforward and modular access to C4-arylated [2.2]paracyclophanes.
View Article and Find Full Text PDFNat Chem
July 2023
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China.
Direct and selective functionalization of hydrocarbon chains is a fundamental problem in synthetic chemistry. Conventional functionalization of C=C double bonds and C(sp)-H bonds provides some solutions, but site diversity remains an issue. The merging of alkene isomerization with (oxidative) functionalization provides an ideal method for remote functionalization, which would provide more opportunities for site diversity.
View Article and Find Full Text PDFNat Chem
June 2023
State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China.
Methods for the enantioselective direct oxygenation of internal alkenes have provided chemists with versatile and powerful toolboxes for the synthesis of optically pure alcohols, one of the most privileged structural motifs. Regioselectivity, however, remains a formidable challenge in the functionalization of internal alkenes. Here we report a palladium-catalysed highly regio- and enantioselective remote 1,n-dioxygenation (n ≥ 4) of internal alkenes with engineered pyridine-oxazoline (Pyox) ligands.
View Article and Find Full Text PDFOrg Biomol Chem
March 2023
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
A palladium-catalysed direct arene C-H fluoroalkoxylation of 4-aryl-pyrrolo[2,3-]pyrimidine derivatives with fluorinated alcohols is described. Highly site-selective mono- or bis-fluoroalkoxylation can be achieved by tuning the reaction conditions, affording various fluoroalkoxylated pyrrolo[2,3-]pyrimidine derivatives in moderate to good yields, which offer rational tailoring of their biological activity for their application in the field of pharmaceutical chemistry.
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