Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines

被引：41

作者：

Chen, Xinzheng ^{[1
]}

Qiu, Shuxian ^{[1
]}

Wang, Sasa ^{[1
]}

Wang, Huifei ^{[1
]}

Zhai, Hongbin ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Guangdong Prov Key Lab Nanomicro Mat Res, Shenzhen 518055, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 30期

关键词：

CIS-TRANS ISOMERIZATION; STEREOSELECTIVE-SYNTHESIS; PHOTOCHEMICAL-REACTIONS; ALKENE ISOMERIZATION; COUPLING REACTION; METAL-COMPLEXES; OLEFINATION; EFFICIENT; MECHANISM; PHOTOISOMERIZATION;

D O I：

10.1039/c7ob00558j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.

引用

页码：6349 / 6352

页数：4

共 52 条

[1] Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo .

CHEMICAL REVIEWS, 2009, 109 (08) :3817-3858

[2] Benzil-tethered precipitons for controlling solubility: A round-trip energy-transfer mechanism in the isomerization of extended stilbene analogues [J].

Ams, Mark R. ;

Wilcox, Craig S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3966-3972

[3] Intramolecularly sensitized precipitons: A model system for application to metal sequestration [J].

Ams, MR ;

Wilcox, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :250-256

[4] PHOTOSENSITIZED CIS-TRANS ISOMERIZATION OF BETA-ALKYLSTYRENES [J].

ARAI, T ;

SAKURAGI, H ;

TOKUMARU, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (07) :2204-2207

[5] PHOTOCHEMICAL ONE-WAY ADIABATIC ISOMERIZATION OF AROMATIC OLEFINS [J].

ARAI, T ;

TOKUMARU, K .

CHEMICAL REVIEWS, 1993, 93 (01) :23-39

[6] UNUSUAL BEHAVIOR OF BETA-TERT-ALKYLSTYRENES IN PHOTOSENSITIZED CIS-TRANS ISOMERIZATION - STRUCTURAL EFFECTS ON TRIPLET ENERGY-TRANSFER [J].

ARAI, T ;

SAKURAGI, H ;

TOKUMARU, K .

CHEMISTRY LETTERS, 1980, (03) :261-264

[7]

Barbero A, 2000, SYNTHESIS-STUTTGART, P1223

[8] Synthetic Control of Retinal Photochemistry and Photophysics in Solution [J].

Bassolino, Giovanni ;

Sovdat, Tina ;

Liebel, Matz ;

Schnedermann, Christoph ;

Odell, Barbara ;

Claridge, Timothy D. W. ;

Kukura, Philipp ;

Fetcher, Stephen P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (06) :2650-2658

[9] ARE PERPENDICULAR ALKENE TRIPLETS JUST 1,2-BIRADICALS - STUDIES WITH THE CYCLOPROPYLCARBINYL CLOCK [J].

CALDWELL, RA ;

ZHOU, LW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2271-2275

[10] Z-Selective Alkene Isomerization by High-Spin Cobalt(II) Complexes [J].

Chen, Chi ;

Dugan, Thomas R. ;

Brennessel, William W. ;

Weix, Daniel J. ;

Holland, Patrick L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :945-955

← 1 2 3 4 5 6 →