Photocatalytic Synthesis of 6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C-P and C-C Bond Formation

被引：1

作者：

Wang, Liping ^{[1
]}

Zhang, Qin ^{[2
]}

Sang, Xiaoyan ^{[1
]}

Ding, Qiuping ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Key Lab Fluorine & Silicon Energy Mat, Key Lab Green Chem Jiangxi Prov,Minist Educ, Nanchang 330022, Peoples R China

[2] Jiangxi Geol Survey Inst, Basic Geol Survey Inst, Nanchang 330201, Peoples R China

来源：

CATALYSTS | 2023年 / 13卷 / 07期

基金：

中国国家自然科学基金;

关键词：

phenanthridine; 2-isocyanobiphenyls; diarylphosphine oxides; radical cyclization; metal-free; CYCLIZATION; ISOCYANIDES; OXIDES;

D O I：

10.3390/catal13071036

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A mild, efficient, photocatalytic synthesis of 6-phosphorylated phenanthridines via tandem radical addition/cyclization/aromatization of 2-isocyanobiphenyls with diarylphosphine oxides is reported. The method features operational simplicity in metal-free conditions, using low-cost Rose Bengal as a catalyst and sustainable air as a terminal oxidant at room temperature and providing the desired products in moderate to good yields.

引用

页数：12

共 50 条

[41] Visible-light-photoredox catalytic C-C, C-N bond formation: Synthesis of pyrazole derivatives via radical ions
Sagir, Hozeyfa
Rai, Pragati
Ibad, Afshan
Ibad, Farah
Siddiqui, I. R.
CATALYSIS COMMUNICATIONS, 2017, 100 : 153 - 156
[42] Synthesis of Imidazo[1,2-f]phenanthridines through Palladium-Catalyzed Intramolecular C-C Bond Formation
Saini, Hitesh Kumar
Dhiman, Shiv
Pericherla, Kasiviswanadharaju
Kumar, Anil
SYNTHESIS-STUTTGART, 2015, 47 (23): : 3727 - 3732
[43] Synthesis of chelating tertiary phosphine oxides via palladium-catalysed C-P bond formation
Zakirova, Gladis G.
Mladentsev, Dmitrii Yu.
Borisova, Nataliya E.
TETRAHEDRON LETTERS, 2017, 58 (35) : 3415 - 3417
[44] Oxidative C(SP2)-P Formation: Direct Construction of C-P Bond on Quinoxalines via Aromatic Phosphorous Oxide
Xiong, Yunkui
Zhang, Jianye
Qi, Liping
Zhang, Yu
Wang, Tao
CHEMISTRYSELECT, 2021, 6 (04): : 657 - 662
[45] Developments towards synthesis of N-heterocycles from amidines via C-N/C-C bond formation
Guo, Wei
Zhao, Mingming
Tan, Wen
Zheng, Lvyin
Tao, Kailiang
Fan, Xiaolin
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2120 - 2141
[46] C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4
Dangel, BD
Godula, K
Youn, SW
Sezen, B
Sames, D
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) : 11856 - 11857
[47] Boryl Radical-Promoted Synthesis of Biaryls and Benzylcarboxylic Acids Methyl Ester via C-C Bond Formation Reactions
Li, Wenduo
Wei, Na'na
Feng, Nan
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (06) : 1853 - 1861
[48] Synthesis of Complex Allylic Esters via C-H Oxidation vs C-C Bond Formation
Vermeulen, Nicolaas A.
Delcamp, Jared H.
White, M. Christina
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) : 11323 - 11328
[49] Reactivity of OsH2Cl2((PPr3)-Pr-i)(2) toward diolefins: New reactions involving C-H and C-C activation and C-C and C-P bond formation processes
Edwards, AJ
Esteruelas, MA
Lahoz, FJ
Lopez, AM
Onate, E
Oro, LA
Tolosa, JI
ORGANOMETALLICS, 1997, 16 (06) : 1316 - 1325
[50] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C/C-O BOND FORMATION
SAMES, D
POLT, R
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 392 - ORGN

← 1 2 3 4 5 →