Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc) and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00503 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Polysubstituted Aromatics via the Pd(II)-Initiated Borono-Catellani Reaction.
Org Lett
March 2025
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China.
Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc) and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.
View Article and Find Full Text PDFSecondary Alkylation of Arenes via the Borono-Catellani Strategy.
J Am Chem Soc
January 2025
Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences, and TaiKang Center for Life and Medical Sciences, Wuhan University, Wuhan 430072, China.
A modular platform technology for the synthesis of α-aryl carbonyl derivatives via Borono-Catellani-type secondary alkylation of arenes is presented. This practical method features a broad substrate scope regarding aryl boronic acid catechol esters, secondary alkyl bromides, and diversified terminating reagents (e.g.
View Article and Find Full Text PDFPractical synthesis of -aryl glycosides redox-neutral Borono-Catellani reaction.
Chem Commun (Camb)
January 2025
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center fo
Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of -aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated -(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner.
View Article and Find Full Text PDFChemoselective Borono-Catellani Arylation for Unsymmetrical Biaryls Synthesis.
Org Lett
May 2019
Sauvage Center for Molecular Sciences, College of Chemistry and Molecular Sciences , Wuhan University, 430072 Wuhan , China.
Reported is the borono-Catellani arylation process for unsymmetrical biaryls synthesis, utilizing the readily available pinacol ester of arylboronic acids, aryl bromides, and olefins as the reactants. The distinct reactivity of arylboronic ester and aryl bromides secures the excellent chemoselectivity in the pivotal arylation step. The reaction is enabled by the cooperative catalysis of Pd(OAc) and the NBE derivative N, with molecular oxygen as the terminal oxidant.
View Article and Find Full Text PDFThe Discovery of a Palladium(II)-Initiated Borono-Catellani Reaction.
Angew Chem Int Ed Engl
June 2018
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
Reported is a novel palladium(II)-initiated Catellani-type reaction that utilizes widely accessible aryl boronic acids as the substrates instead of aryl halides, thereby greatly expanding the existing scope of this powerful transformation. This borono-Catellani reaction was promoted by cooperative catalysis between Pd(OAc) and the inexpensive 5-norbornene-2-carbonitrile. Practicality is the striking feature of the reaction: it is run open to air at ambient temperature and no phosphine ligand is needed.
View Article and Find Full Text PDF