Metal‐free and One‐pot for the Synthesis of the Indolo[2,1‐a]isoquinoline Aldehyde via Free Radical Cascade Pathway followed Direct Hydrolyzation

2022 ◽  
Author(s):  
YouLu Pan ◽  
Xiaomeng Gong ◽  
Rongrong Hao ◽  
Shenxin Zeng ◽  
Jinghao Xu ◽  
...  
Keyword(s):  
Free Radical ◽  
One Pot ◽  
Metal Free ◽  
Radical Cascade

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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...

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.

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.

An Easy Access to Sulfur Derivatives of 6,8-Dioxabicyclo[3.2.1]octanes, Naturally Abundant Scaffolds

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2624-2630 ◽  
Author(s):  
Elena Schmidt ◽  
Ivan Bidusenko ◽  
Igor Ushakov ◽  
Nadezhda Protsuk ◽  
Boris Trofimov
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Transition Metal ◽  
Uv Irradiation ◽  
Radical Reaction ◽  
Easy Access ◽  
Free Radical Reaction ◽  
One Pot ◽  
Metal Free ◽  
Derivatives Of

Sulfur derivatives of 6,8-dioxabicyclo[3.2.1]octanes related to a number of natural products have been synthesized by the click hydrothiolation (AIBN or UV irradiation) of 7-methylene-6,8-dioxabicy­clo[3.2.1]octanes, assembled from acetylene and ketones in a one-pot transition-metal-free synthetic operation. An unusual feature of this free-radical reaction is that it is accelerated in the presence of bases due to involvement of the latter in a competition between the thiol addition and proton-catalyzed isomerization of the starting bicyclooctanes.

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 Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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.

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...

A NaSO2CF3/NaBrO3-mediated bromotrifluoromethylation of enyne via free-radical cascade processes

2018 ◽  
Vol 5 (19) ◽  
pp. 2856-2859 ◽  
Author(s):  
Xiao-Jie Shang ◽  
Dong Liu ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free ◽  
Radical Cascade ◽  
Cascade Processes

A NaBrO3-induced radical bromotrifluoromethylation of enynes with NaSO2CF3 was developed. This method allows a transition-metal free, highly selective and step-economic access to diverse bromotrifluoromethylated five- and six-membered heterocycles.

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