An Improved Synthesis of Natural Product Inspired Chromenopyrrolizines and Chromenoindolizines Scaffolds: Rapid Access to the Diverse Pyrrolizine Analogs of Aza-Medicarpin and Tetracyclic Isolamellarin Core through a General Base and Metal Free Strategy

2016 ◽  
Vol 89 (11) ◽  
pp. 1331-1340 ◽  
Author(s):  
Tabrez Khan ◽  
Virendra Kumar ◽  
Oindreela Das
Keyword(s):  
Natural Product ◽  
Metal Free ◽  
General Base ◽  
Rapid Access

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

Metal-free trifluoroethylation of activated alkenes: rapid access to construct fluorinated 3,3-disubstituted 2-oxindoles

Tetrahedron ◽  
2015 ◽  
Vol 71 (44) ◽  
pp. 8416-8423 ◽  
Author(s):  
Wen-Peng Mai ◽  
Bin Sun ◽  
Guan-Sheng Qian ◽  
Jin-Wei Yuan ◽  
Pu Mao ◽  
...  
Keyword(s):  
Metal Free ◽  
Rapid Access

ChemInform Abstract: Metal-Free Trifluoroethylation of Activated Alkenes: Rapid Access to Construct Fluorinated 3,3-Disubstituted 2-Oxindoles.

ChemInform ◽  
2016 ◽  
Vol 47 (5) ◽  
pp. no-no
Author(s):  
Wen-Peng Mai ◽  
Bin Sun ◽  
Guan-Sheng Qian ◽  
Jin-Wei Yuan ◽  
Pu Mao ◽  
...  
Keyword(s):  
Metal Free ◽  
Rapid Access

ChemInform Abstract: Scalable, Transition-Metal-Free Direct Oxime O-Arylation: Rapid Access to O-Arylhydroxylamines and Substituted Benzo[b]furans.

ChemInform ◽  
2014 ◽  
Vol 46 (3) ◽  
pp. no-no ◽  
Author(s):  
Hongyin Gao ◽  
Qing-Long Xu ◽  
Craig Keene ◽  
Laszlo Kuerti
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Rapid Access

Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 763-768
Author(s):  
Jiarun Liu ◽  
Jiancheng Huang ◽  
Kuiyong Jia ◽  
Tianxing Du ◽  
Changyin Zhao ◽  
...  
Keyword(s):  
Oxidative Dearomatization ◽  
Aromatic Ketones ◽  
Metal Free ◽  
Rapid Access ◽  
Oxoammonium Salt

A metal-free oxidative dearomatization of indoles with aromatic ketones mediated by TEMPO oxoammonium salt is described. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones in the presence of H2SO4, affording the corresponding 2,2-disubstituted indolin-3-ones in good yields.

A transition metal-free approach to a regioselective total synthesis of the natural product derivative 6-methylellipticine, a potent anticancer agent

2019 ◽  
Vol 60 (51) ◽  
pp. 151309 ◽  
Author(s):  
Song-Bo Lin ◽  
Wan-Wan Wang ◽  
Jin-Peng Meng ◽  
Xi-Wang Li ◽  
Jun Wu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Natural Product ◽  
Anticancer Agent ◽  
Metal Free

One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities

2022 ◽  
Author(s):  
Shiqiang Li ◽  
Wei Yan ◽  
Liu-Jun He ◽  
Ming Zhang ◽  
Dianyong Tang ◽  
...  
Keyword(s):  
Natural Product ◽  
Cascade Reaction ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Anti Cancer

A post-Ugi/diastereoselective cascade reaction was developed to construct naturally existing spiroindolines via a facile and metal-free one-pot protocol. During the construction, a new C-C bond was formed through a selective...

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