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Literature DB >> 30945447

Oxidative Coupling of 3-Oxindoles with Indoles and Arenes.

Houng Kang¹, Adriana L Jemison¹, Erin Nigro¹, Marisa C Kozlowski¹.

Abstract

A highly efficient method for the oxidative coupling of 2-substituted 3-oxindoles with aromatic compounds to form 2,2-disubstituted indolin-3-ones with broad scope is described. This work utilized oxygen as the terminal oxidant and a base-metal catalyst under mild conditions instead of toxic/precious-metal reagents and higher-molecular-weight oxidants. Quaternary structures were produced in modest-to-excellent yields (up to 96 %) without prefunctionalization.

Entities: CellLine Chemical Disease Species

Keywords: catalysis; coinage metals; oxidative coupling; oxygen; sustainable

Year: 2019 PMID： 30945447 PMCID： PMC6703824 DOI： 10.1002/cssc.201900438

Source DB: PubMed Journal: ChemSusChem ISSN： 1864-5631 Impact factor: 8.928

17 in total

Review 1. Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations.

Authors: Chao Liu; Jiwen Yuan; Meng Gao; Shan Tang; Wu Li; Renyi Shi; Aiwen Lei
Journal: Chem Rev Date: 2015-11-11 Impact factor: 60.622

2. Gold-catalyzed transformation of 2-alkynyl arylazides: efficient access to the valuable pseudoindoxyl and indolyl frameworks.

Authors: Alexander Wetzel; Fabien Gagosz
Journal: Angew Chem Int Ed Engl Date: 2011-06-24 Impact factor: 15.336

3. Indole alkaloids from Cephalanceropsis gracilis.

Authors: Pei-Lin Wu; Yu-Lin Hsu; Chen-Wei Jao
Journal: J Nat Prod Date: 2006-10 Impact factor: 4.050

4. Mechanistic investigations on the reaction between 1,2-dioxines and bulky stabilized phosphorus ylides: an efficient route to closely related cyclopropane stereoisomers.

Authors: T D Avery; G Fallon; B W Greatrex; S M Pyke; D K Taylor; E R Tiekink
Journal: J Org Chem Date: 2001-11-30 Impact factor: 4.354

5. Study of the addition of Grignard reagents to 2-aryl-3H-indol-3-ones.

Authors: Yahua Liu; William W McWhorter
Journal: J Org Chem Date: 2003-04-04 Impact factor: 4.354

6. Notoamide O, a structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp.

Authors: Sachiko Tsukamoto; Hideharu Umaoka; Kohei Yoshikawa; Tsuyoshi Ikeda; Hiroshi Hirota
Journal: J Nat Prod Date: 2010-08-27 Impact factor: 4.050

7. Isatisine A, a novel alkaloid with an unprecedented skeleton from leaves of Isatis indigotica.

Authors: Ji-Feng Liu; Zhi-Yong Jiang; Rui-Rui Wang; Yong-Tang Zheng; Ji-Jun Chen; Xue-Mei Zhang; Yun-Bao Ma
Journal: Org Lett Date: 2007-09-13 Impact factor: 6.005

8. Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters.

Authors: Ren-Rong Liu; Shi-Chun Ye; Chuan-Jun Lu; Gui-Lin Zhuang; Jian-Rong Gao; Yi-Xia Jia
Journal: Angew Chem Int Ed Engl Date: 2015-08-05 Impact factor: 15.336

Oxidative Coupling of 3-Oxindoles with Indoles and Arenes.

Review 1. Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations.

2. Gold-catalyzed transformation of 2-alkynyl arylazides: efficient access to the valuable pseudoindoxyl and indolyl frameworks.

3. Indole alkaloids from Cephalanceropsis gracilis.

4. Mechanistic investigations on the reaction between 1,2-dioxines and bulky stabilized phosphorus ylides: an efficient route to closely related cyclopropane stereoisomers.

5. Study of the addition of Grignard reagents to 2-aryl-3H-indol-3-ones.

6. Notoamide O, a structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp.

7. Isatisine A, a novel alkaloid with an unprecedented skeleton from leaves of Isatis indigotica.

8. Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters.

9. Synthesis of pseudo-indoxyl derivatives via sequential Cu-catalyzed S(N)Ar and Smalley cyclization.

10. Selective oxidative homo- and cross-coupling of phenols with aerobic catalysts.

1. Catalytic Oxidative Coupling of Phenols and Related Compounds.

2. Cyanomethylation of Substituted Fluorenes and Oxindoles with Alkyl Nitriles.