A Pd-catalyzed route to carborane-fused boron heterocycles.

Autor: Zhu M; Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China xinmu@ecust.edu.cn., Wang P; Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China xinmu@ecust.edu.cn., Wu Z; Functional Coordination Material Group-Frontier Research Center, Songshan Lake Materials Laboratory, Dongguan Dongguan 523808 Guangdong China zouchao@sslab.org.cn., Zhong Y; Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China xinmu@ecust.edu.cn., Su L; School of Biotechnology, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China., Xin Y; Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China xinmu@ecust.edu.cn., Spokoyny AM; Department of Chemistry and Biochemistry, University of California, Los Angeles 607 Charles E. Young Drive East Los Angeles California 90095 USA.; California NanoSystems Institute (CNSI), University of California, Los Angeles Los Angeles California 90095 USA spokoyny@chem.ucla.edu., Zou C; Functional Coordination Material Group-Frontier Research Center, Songshan Lake Materials Laboratory, Dongguan Dongguan 523808 Guangdong China zouchao@sslab.org.cn., Mu X; Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China xinmu@ecust.edu.cn.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2024 May 28; Vol. 15 (27), pp. 10392-10401. Date of Electronic Publication: 2024 May 28 (Print Publication: 2024).
DOI: 10.1039/d4sc02214a
Abstrakt: Due to the expanding applications of icosahedral carboranes in medicinal and materials chemistry research, their functionalizations have become one of the central themes in boron-rich cluster chemistry. Although several strategies for incorporating nitrogen-containing nucleophiles on a single boron vertex of the icosahedral carboranes (C 2 B 10 H 12 ) have been developed, methods for preparing clusters with vicinal B-N moieties are still lacking. The steric bulk of icosahedral carboranes and disparate electronic and steric nature of the N-containing groups have rendered the vicinal diamination challenging. In this article, we show how a developed Pd-catalyzed process is used to incorporate an array of NH-heterocycles, anilines, and heteroanilines with various electronic and steric profiles onto the vicinal boron vertices of a meta -carborane cluster via sequential or one-pot fashion. Importantly, oxidative cyclizations of the cross-coupling products with indoles and pyrroles appended to boron vertices generate a previously unknown class of all-boron-vertex bound carborane-fused six- and seven-membered ring heterocycles. Photophysical studies of the meta -carborane-fused heterocycles show that these structures can exhibit luminescence with high quantum yields and are amenable to further manipulations.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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