Cited by Cu/Pd-Catalyzed Domino Carbonylative Synthesis of Polycyclic Carbonyl-Containing Quinolin-2(1<i>H</i>)-one Scaffolds from α-Bromocarbonyls

Palladium-Catalyzed Carbonylative Synthesis of Polycyclic 3,4-Dihydroquinolin-2(1H)-one Scaffolds Containing Perfluoroalkyl and Carbonyl Units DOI

Shangyuan Wang,

Jiajun Zhao, Jun Ying

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5314 - 5318

Published: July 6, 2023

A palladium-catalyzed one-pot two-step radical mediated carbonylative cyclization of 1,7-enynes with perfluoroalkyl iodides and Mo(CO)6 has been developed for the construction polycyclic 3,4-dihydroquinolin-2(1H)-one scaffolds. This method realizes a facile synthesis various derivatives containing carbonyl units in high yields. Moreover, modifications several bioactive molecules were demonstrated using this protocol.

Language: Английский

Citations

Palladium-Catalyzed Cascade Carbonylative Synthesis of Perfluoroalkyl and Carbonyl-Containing 3,4-Dihydroquinolin-2(1H)-one Derivatives DOI

Shangyuan Wang,

Jiangjie Zhang,

Jian‐Shu Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(48), P. 8843 - 8847

Published: Nov. 24, 2022

A palladium-catalyzed cascade radical cyclization and carbonylation of 1,7-enynes with perfluoroalkyl iodides alcohols has been described. This procedure provides a facile efficient approach for the construction 3,4-dihydroquinolin-2(1H)-one skeletons by using benzene-1,3,5-triyl triformate (TFBen) as CO source. method enables incorporation both carbonyl units into skeletons, producing variety derivatives in moderate to high yields excellent E/Z selectivity.

Language: Английский

Citations

Demethylenative cyclization of 1,7-enynes using α-amino radicals as a traceless initiator enabled by Cu(i)-photosensitizers DOI

Qinfang Jiang,

Hanyang Bao,

Yun Peng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(50), P. 6399 - 6402

Published: Jan. 1, 2024

A rare type of demethylenative intramolecular cyclization 1,7-enynes to access quinoline-2-(1

Language: Английский

Citations

Palladium-Catalyzed Domino Cyclization and C-H Amination of 1,7-Enynes Toward N-containing Fused Quinolin-2(1H)-ones DOI

Jiajun Zhao, Shuwei Li, Linqi Wang

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel palladium-catalyzed domino radical cyclization and C–H amination of 1,7-enynes has been developed for the rapid establishment N-containing fused quinolin-2(1 H )-one scaffolds.

Language: Английский

Citations

Gold(I)-catalyzed tandem cyclization/peroxidation of 2-alkynyl-1-carbonylbenzenes with TBHP DOI

Lang Chen,

Q.-X. Ni,

Yan Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A gold(I)-catalyzed tandem cyclization/peroxidation of 2-alkynyl-1-carbonylbenzenes with tert-butyl hydroperoxide (TBHP) has been successfully developed to access 1-peroxidized 1H-isochromene derivatives in moderate good yields. The use one the resultant 1H-isochromenes (3a) for construction phenyl(8-phenylbicyclo[4.2.0]octa-1(6),2,4,7-tetraen-7-yl)methanone (4), phenyl(3-phenyl-1,3-dihydroisobenzofuran-1-yl)methanone (5) and 2-(2-benzoylphenyl)-1-phenylethan-1-one (6) also investigated, respectively.

Language: Английский

Citations

Nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides DOI

Yanling Zhang, Zhiguo Zhang, Yuanyuan Hu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(41), P. 8049 - 8053

Published: Jan. 1, 2022

In this text, we describe a nickel-catalyzed cyanation reaction of aryl/alkenyl halides with isocyanides, affording nitriles in moderate to good yields broad functional group tolerance.

Language: Английский

Citations

Formation of cyclopenta[c]quinolines through visible-light-induced photoredox cascade bis-annulations of 1,7-enynes with sulfoxonium ylides DOI

Ning Xian,

Guo‐Jun Deng, Huawen Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(37), P. 7618 - 7622

Published: Jan. 1, 2024

A novel visible-light-driven photoredox-catalyzed cascade bicyclization of 1,7-enynes with aqueous sulfoxonium ylides is reported. The reaction highly chemoselective three new C-C bonds, two rings, and an all-carbon quaternary stereocenter constructed in a one-pot fashion. This mild protocol features remarkably broad substrate scope good functional group tolerance, providing general practical approach to access various cyclopenta[

Language: Английский

Citations

Approach to Access Benzo[j]phenanthridinones from 1,7-Enynes and Aryldiazonium Salts via a Domino Radical Relay Process Enabled by a P/N-Heteroleptic Cu(I)-Photosensitizer DOI

Siwei Xiang,

Q.-X. Ni,

Qian Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13248 - 13261

Published: Aug. 24, 2023

A mild approach for the synthesis of benzo[j]phenanthridin-6(5H)-one derivatives from 1,7-enynes and aryldiazonium salts has been successfully developed involving a domino radical relay process enabled by heteroleptic Cu(I)-photosensitizer under visible-light-driven photocatalytic conditions. Mechanistic studies disclosed that oxidative quenching excited state PS 4 with via an SET generated aryl radicals, which could play initiator-terminator dual role within whole process, namely, at initial step acting as donor to trigger addition olefin moieties while final stage serving acceptor complete cyclization.

Language: Английский

Citations

P/N-heteroleptic Cu(i)-photosensitizer-catalyzed domino radical relay annulation of 1,6-enynes with aryldiazonium salts DOI

Qian Liu,

Q.-X. Ni,

Yan Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(39), P. 7960 - 7967

Published: Jan. 1, 2023

A visible-light driven photocatalytic construction of benzo[b]fluorenones from 1,6-enynes and aryldiazonium salts has been achieved via a P/N-heteroleptic Cu(I)-photosensitizer-catalyzed domino radical relay annulation process. Preliminary mechanistic studies revealed that the aryl radicals in situ generated with excited state Cu(I)-photosensitizer played dual role initiator terminator concise highly fused benzo[b]fluorenone scaffold.

Language: Английский

Citations

Ligand- and Substrate-Controlled Chemodivergent Pd-Catalyzed Annulations of Cyclic β-Keto Esters with 3-Aryl-2H-azirines DOI

Fang Xie, Yajun Sun,

Hanghang Song

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 24(1), P. 268 - 273

Published: Dec. 10, 2021

Chemodivergent Pd-catalyzed annulations of cyclic β-keto esters with 3-aryl-2H-azirines have been developed to provide rapid access eight-membered ring lactams, bicyclic 3,4-dihydro-2H-pyrrole derivatives, and (E)-methyl [2-(2-oxocyclohexylidene)-2-phenylethyl]carbamates high efficiency. The chemoselectivity can be determined by tuning the mono- or bisphosphine ligands as well substrate structure esters.

Language: Английский

Citations