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Zero-Valent Copper Catalysis Enables Regio- and Stereoselective Difunctionalization of Alkynes.
Angew Chem Int Ed Engl
January 2025
Jain University - Ramanagara Campus, Centre for Nano and Material Sciences, Jakkasandra Post Kanakapura Taluk, Ramanagara-562112, Bangalore, 562112, Bangalore, INDIA.
The development of a metallic copper-based catalyst system remains a significant challenge. Herein, we report the synthesis of highly stable, active, and reusable Cu0 catalyst for the carboboration of alkynes using carbon electrophiles and bis(pinacolato)diboron (B2pin2) as chemical feedstocks to afford di- and trisubstituted vinylboronate esters in a regio- and stereoselective manner with appreciable turnover number (TON) of up to 2535 under mild reaction conditions. This three-component coupling reaction works well with a variety of substituted electrophiles and alkynes with broad functional group tolerance.
View Article and Find Full Text PDFStructure-Reactivity Relationship of Zeolite-Confined Rh Catalysts for Hydroformylation of Linear α-Olefins.
J Am Chem Soc
January 2025
Engineering Research Center of Advanced Rare-Earth Materials of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.
Substituting the molecular metal complexes used in the industrial olefin hydroformylation process is of great significance in fundamental research and practical application. One of the major difficulties in replacing the classic molecular metal catalysts with supported metal catalysts is the low chemoselectivity and regioselectivity of the supported metal catalysts because of the lack of a well-defined coordination environment of the metal active sites. In this work, we have systematically studied the influences of key factors (crystallinity, alkali promoters, etc.
View Article and Find Full Text PDFMo(0) carbonyl complexes bearing the bis(3,5-dimethylpyrazole) ligand: catalysis of the regioselective [2 + 2 + 2] cycloaddition of terminal alkynes to synthesize 1,3,5-isomers.
Dalton Trans
January 2025
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721302 India.
The reaction between 1,3-bis(3,5-dimethylpyrazolylmethyl)hexahydropyrimidine L and Mo(CO) in CHCN at 130 °C afforded a binuclear Mo(0) complex 1 containing a new macrocycle formed upon C-N bond cleavage in L in good yield. Conversely, a clean reaction takes place between L and [Mo(CO)(COD)] in THF at 60 °C to give a new metalloligand complex [Mo(CO)(κ-,-L)] 2 containing a spectator pyrazole arm in 83% yield. Their structures were determined by X-ray diffraction methods, and a plausible mechanism is proposed for the C-N bond cleavage leading to complex 1.
View Article and Find Full Text PDFCatalyst Improved Stereoselectivity and Regioselectivity Control to Access Completely Alternating Poly(lactic-co-glycolic acid) with Enhanced Properties.
Angew Chem Int Ed Engl
December 2024
Key Laboratory of Photoelectric Conversion and Utilization of Solar Energy, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, China.
The poly(lactic-co-glycolic acid) (PLGA) with completely alternating sequence has attracted growing attention as an ideal candidate in controlled drug delivery. However, the approach to completely alternating PLGA remains a challenge. Herein, we report the successful synthesis of completely alternating PLGA via highly regioselective and stereoselective ring-opening polymerization.
View Article and Find Full Text PDFEnhanced Antitumor Immunity of a Globo H-Based Vaccine Enabled by the Combination Adjuvants of 3D-MPL and QS-21.
Angew Chem Int Ed Engl
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
Globo H, a specific carbohydrate antigen overexpressed on various human malignancies, has attracted considerable interest as an antigenic target for anticancer vaccine development. Despite several Globo H-based carbohydrate vaccines that have been designed, efficient access to Globo H hexasaccharide antigen and development of powerful adjuvants for enhancing antitumor immunity remain challenging. Herein, we reported a streamlined chemoenzymatic approach to prepare this hexasaccharide antigen, relying on chemical synthesis of Gb5 pentasaccharide by a stereoconvergent [2+3] strategy and subsequent enzymatic α-fucosylation to easily install α1,2-fucose residue.
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