The photoredox/PPh-mediated cyclization of 2-isocyanobiaryls has been developed. A substantial range of functional-group-rich phenanthridine derivatives were synthesized at room temperature in a highly selective and atom-economic manner. Mechanistic studies suggested that the cyclization process is probably mediated both by PhP radical cation with key 1,2-hydride transfer and hydrogen atom generated through O-H bond homolytic cleavage of PhP-OH radical intermediate.
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http://dx.doi.org/10.1021/acs.orglett.3c03744 | DOI Listing |
J Org Chem
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17, Third Section, South Renmin Road, Chengdu 610041, P. R. China.
A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.
View Article and Find Full Text PDFOrg Lett
December 2023
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, China.
The photoredox/PPh-mediated cyclization of 2-isocyanobiaryls has been developed. A substantial range of functional-group-rich phenanthridine derivatives were synthesized at room temperature in a highly selective and atom-economic manner. Mechanistic studies suggested that the cyclization process is probably mediated both by PhP radical cation with key 1,2-hydride transfer and hydrogen atom generated through O-H bond homolytic cleavage of PhP-OH radical intermediate.
View Article and Find Full Text PDFJ Org Chem
December 2023
Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.
Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis of 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, and good functional group compatibility under metal- and oxidant-free reaction conditions.
View Article and Find Full Text PDFJ Org Chem
July 2023
Postdoctoral Mobile Station of Basic Medical Sciences, Hengyang Medical School, University of South China, Hengyang 421001, China.
A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodonium ylides was established for the synthesis of 6-arylated phenanthridines. This is the first example of employing iodonium ylides as aryl radical sources in a visible-light-induced radical cascade cyclization reaction.
View Article and Find Full Text PDFOrg Biomol Chem
April 2022
School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram (IISER-TVM), 695551, India.
We herein report the first photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides. This simple protocol operates under mild reaction conditions and affords 6-alkyl phenanthridines in good yields. To elucidate the reaction mechanism, Stern-Volmer quenching studies were carried out and these studies revealed that the photocatalyst is not directly involved in a single electron transfer process with the alkyl iodide.
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