An increasing number of chemical reactions are being employed for bio-orthogonal ligation of detection labels to protein-bound functional groups. Several of these strategies, however, are limited in their application to pure proteins and are ineffective in complex biological samples such as cell lysates. Here we present the palladium-catalyzed oxidative Heck reaction as a new and robust bio-orthogonal strategy for linking functionalized arylboronic acids to protein-bound alkenes in high yields and with excellent chemoselectivity even in the presence of complex protein mixtures from living cells. Advantageously, this reaction proceeds under aerobic conditions, whereas most other metal-catalyzed reactions require inert atmosphere.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4159585 | PMC |
http://dx.doi.org/10.1002/cbic.201300714 | DOI Listing |
Org Lett
December 2024
Department of Chemistry, Indian Institute of Technology, Kharagpur, West Bengal 721302, India.
Development of metal-free conversion of naturally abundant phenols and anilines to the corresponding olefins remains a formidable challenge. The current state of the art relies on the TM-catalyzed Heck coupling of activated phenols (triflates, tosylates, and more) with the olefins. While these advancements are promising, the reaction suffers from branch vs linear selectivity and requires an expensive TM-ligand combination, hazardous organotin reagents, and very high reaction temperature.
View Article and Find Full Text PDFJ Org Chem
December 2024
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent to the allyl group. A selective allylic oxidation of the coupling products was accomplished using DDQ in the presence of silica to furnish the chalcones.
View Article and Find Full Text PDFChem Sci
December 2024
School of Chemical Engineering and Light Industry, Guangdong University of Technology No. 100 Waihuan Xi Road Guangzhou Higher Education Mega Center Guangzhou 510006 China
The oxidative Heck reaction of strongly coordinating heterocycles with internal olefins often led to elusive reactivity and regioselectivity. Herein, by judicious choice of X-type directing groups under Ru(ii) catalysis, we achieved the regioselective oxidative Heck reaction of strongly coordinating heterocycles with sterically demanding internal olefins. It was postulated that the "match/mismatch effect" of sterically demanding internal olefins as coupling partners and subsequent kinetically favoured Michael addition or oxidative aromatization act as driving forces to facilitate the desired reactivity and site-selectivity.
View Article and Find Full Text PDFRSC Med Chem
October 2024
Research Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University 11 Arany Janos str RO-400028 Cluj-Napoca Romania +40 264 593833.
New -substituted AB-type phenothiazinyl porphyrins and ferrocenylvinyl phenothiazinyl porphyrin were synthesised by Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, respectively. The free porphyrins were further used in the synthesis of new indium(iii) or zinc(ii) porphyrin complexes. All porphyrins exhibit red fluorescence emission in solution, a property that remains unimpaired following internalisation in ovarian A2780 cancer cells, as evidenced by fluorescence microscopy images.
View Article and Find Full Text PDFNat Commun
November 2024
Engineering Research Center of Sichuan-Tibet Traditional Medicinal Plant, College of Chemistry and Chemical Engineering, Chengdu University, Chengdu, China.
Carbon-silicon-switch strategy, replacing one specific carbon atom in organic molecules with a silicon, has garnered significant interest for developing new functional molecules. However, the influence of a reaction regarding its selectivity and reactivity by carbon-silicon-switch strategy has far less been investigated. Here we discover an unusual carbon-silicon-switch effect in the enantioselective construction of silicon-stereogenic center.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!