N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[d]oxazoles, Benzo[d]thiazoles and 1,2-Disubstituted Benzo[d]imidazoles

被引：18

作者：

Zhou, Quan ^{[1
]}

Liu, Shu ^{[2
]}

Ma, Ming ^{[2
]}

Cui, He-Zhen ^{[1
]}

Hong, Xi ^{[1
]}

Huang, Shuang ^{[1
]}

Zhang, Jing-Fan ^{[1
]}

Hou, Xiu-Feng ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China

[2] Shanghai Entry Exit Inspect & Quarantine Bur, Tech Ctr Ind Product & Raw Mat Inspect & Testing, Shanghai 200135, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 06期

基金：

美国国家科学基金会;

关键词：

N-heterocyclic carbene; organocatalysis; aerobic oxidation; cyclization; benzazoles; ACTIVATED PHOTOREDOX CATALYSIS; C-H ARYLATION; SCHIFFS BASES; BENZOXAZOLE DERIVATIVES; BENZIMIDAZOLE DERIVATIVES; SELECTIVE SYNTHESIS; ALZHEIMERS-DISEASE; POWERFUL CATALYST; COUPLING REACTION; ROOM-TEMPERATURE;

D O I：

10.1055/s-0036-1591524

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N- Heterocyclic carbene (NHC), generated in situ from easily available N- heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[d]oxazoles, 2-substituted benzo[d]thiazoles, and 1,2-disubstituted benzo[d]imidazoles.

引用

页码：1315 / 1322

页数：8

共 100 条

[21] Cui LJ, 2011, CHINESE J ORG CHEM, V31, P672
[22] Novel 18F-Labeled Benzoxazole Derivatives as Potential Positron Emission Tomography Probes for Imaging of Cerebral β-Amyloid Plaques in Alzheimer's Disease
Cui, Mengchao
Ono, Masahiro
Kimura, Hiroyuki
Ueda, Masashi
Nakamoto, Yuji
Togashi, Kaori
Okamoto, Yoko
Ihara, Masafumi
Takahashi, Ryosuke
Liu, Boli
Saji, Hideo
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (21) : 9136 - 9145
[23] NHC Catalyzed Oxidations of Aldehydes to Esters: Chemoselective Acylation of Alcohols in Presence of Amines
De Sarkar, Suman
Grimme, Stefan
Studer, Armido
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) : 1190 - +
[24] Nature's hydrides: rapid reduction of halocarbons by folate model compounds
Denk, Michael K.
Milutinovic, Nicholas S.
Marczenko, Katherine M.
Sadowski, Natalie M.
Paschos, Athanasios
[J]. CHEMICAL SCIENCE, 2017, 8 (03) : 1883 - 1887
[25] Synthesis and reactivity of subvalent compounds Part 11. Oxidation, hydrogenation and hydrolysis of stable diamino carbenes
Denk, MK
Rodezno, JM
Gupta, S
Lough, AJ
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 242 - 253
[26] Copper-catalyzed arylation of heterocycle C-H bonds
Do, Hien-Quang
Daugulis, Olafs
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12404 - +
[27] An Efficient Synthesis of 2-Substituted Benzoxazoles via RuCl3•3H2O Catalyzed Tandem Reactions in Ionic Liquid
Fan Xuesen
He Yan
Wang Yangyang
Zhang Xinying
Wang Jianji
[J]. CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (04) : 773 - 777
[28] Organocatalyzed Anodic Oxidation of Aldehydes
Finney, Eric E.
Ogawa, Kelli A.
Boydston, Andrew J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12374 - 12377
[29] Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
Flanigan, Darrin M.
Romanov-Michailidis, Fedor
White, Nicholas A.
Rovis, Tomislav
[J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9307 - 9387
[30] Synthesis of Annidines and Benzoxazoles from Activated Nitriles with Ni(0) Catalysts
Garduno, Jorge A.
Garcia, Juventino J.
[J]. ACS CATALYSIS, 2015, 5 (06): : 3470 - 3477

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