Metal-free radical cascade dichloromethylation of activated alkenes using CH2Cl2: highly selective activation of the C–H bond

RSC Advances ◽  
2014 ◽  
Vol 4 (110) ◽  
pp. 64855-64859 ◽  
Author(s):  
Yunfei Tian ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Cascade Process ◽  
Selective Activation ◽  
Metal Free ◽  
Efficient Access ◽  
Radical Cascade

A dicumyl peroxide-initiated highly selective activation of the (sp3)C–H bond in dichloromethane (DCM, CH2Cl2) has been achieved, which allows efficient access to dichloronated oxindoles via a free-radical cascade process.

Metal-Free Cascade Methylation/Cyclization of N-Alkyl-N-methacryloylbenzamides with Dicumyl Peroxide

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 617-620 ◽  
Author(s):  
Yan-Ning Niu ◽  
Xiao-Feng Xia ◽  
Yuan Yuan
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Metal Free ◽  
Wide Range ◽  
Radical Cascade ◽  
Convenient Access

A metal-free radical cascade methylation/cyclization of a wide range of N-alkyl-N-methacryloylbenzamides by using dicumyl peroxide as the methylating reagent provides a convenient access to a series of methylated isoquinoline-1,3-diones in moderate yields.

Transition-metal-free oxidative carboazidation of acrylamides via cascade C–N and C–C bond-forming reactions

2014 ◽  
Vol 12 (25) ◽  
pp. 4329-4334 ◽  
Author(s):  
Jun Qiu ◽  
Ronghua Zhang
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Efficient Method ◽  
Bond Formation ◽  
Cascade Process ◽  
Metal Free ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Radical Cascade ◽  
Novel Strategy

A novel transition-metal-free oxidative carboazidation of acrylamides using inexpensive NaN3 and K2S2O8 was achieved, which not only provided an efficient method to prepare various N3-substituted oxindoles, but also represented a novel strategy for C–N and C–C bond formation via a free-radical cascade process.

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C

Synthesis ◽  
2020 ◽  
Author(s):  
Luis D. Miranda ◽  
Jazmín García-Ramírez
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Cyclization ◽  
Dicumyl Peroxide ◽  
Cyclization Process ◽  
Radical Cascade ◽  
Oxidative Radical Cyclization

AbstractAn efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N-3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.

Metal-free radical cascade chloromethylation of unactivated alkenes: synthesis of polychloro-substituted indolines

2018 ◽  
Vol 16 (32) ◽  
pp. 5752-5755 ◽  
Author(s):  
Changduo Pan ◽  
Du Gao ◽  
Zhenkun Yang ◽  
Chao Wu ◽  
Jin-Tao Yu
Keyword(s):  
Free Radical ◽  
Metal Free ◽  
Radical Cascade

The di- and trichloromethylation of N-allyl anilines with CH2Cl2, CHCl3 and CCl4 was developed, leading to di- and trichloromethylated indolines.

Metal-free radical C–H methylation of pyrimidinones and pyridinones with dicumyl peroxide

2017 ◽  
Vol 19 (4) ◽  
pp. 919-923 ◽  
Author(s):  
Pei-Zhi Zhang ◽  
Jian-An Li ◽  
Ling Zhang ◽  
Adedamola Shoberu ◽  
Jian-Ping Zou ◽  
...  
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Metal Free

A method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide under metal-free conditions is introduced. A 50 g-scale reaction could be performed safely. The product was separated by crystallization and the byproducts were recovery by distillation.

Synthesis of Indolo[2,1-α]isoquinoline Derivatives via Metal-free Radical Cascade Cyclization

2021 ◽  
Author(s):  
Jianzhong Chen ◽  
Hu Xu-yang ◽  
Haifeng Xu ◽  
Qiang Chen ◽  
You-lu Pan
Keyword(s):  
Free Radical ◽  
Core Structure ◽  
Metal Free ◽  
Cascade Cyclization ◽  
Radical Cascade ◽  
Isoquinoline Derivatives

In the present studies, we described a convenient and efficient protocol for the synthesis of the indolo[2,1-]isoquinoline core structure through the reaction of 2-aryl-N-acryloyl indoles and aryl or alkyl -keto...

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