Transition-metal free C(sp2)–C(sp2) bond formation: arylation of 4-aminocoumarins using arynes as an aryl source

2019 ◽  
Vol 17 (40) ◽  
pp. 9014-9025 ◽  
Author(s):  
Abhilash Sharma ◽  
Pranjal Gogoi
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Single Step ◽  
Metal Catalyst ◽  
Metal Free ◽  
Synthetic Strategy

A mild, efficient and transition-metal free synthetic strategy has been developed for the α-arylation of 4-aminocoumarins using arynes as an aryl source. This synthetic strategy proceeds via C(sp2)–C(sp2) bond formation between 4-aminocoumarins and aryne precursors in a single step in the absence of a metal-catalyst.

Synthesis of 6-substituted indoloquinazolinones from arynes and 2-acyl-4-quinazolinones: a transition-metal free C–N and C–C bond formation strategy

2020 ◽  
Vol 44 (41) ◽  
pp. 17938-17953
Author(s):  
Abhilash Sharma ◽  
Pranjal Gogoi
Keyword(s):  
Transition Metal ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Reaction Vessel ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Single Reaction

A versatile transition-metal free synthetic strategy has been developed for the direct synthesis of 6-substituted indoloquinazolinones from 2-acyl-4-quinazolinones and aryne precursors. This cascade strategy proceeds via successive C–N and C–C bond formation in a single reaction vessel.

scholarly journals Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guogang Deng ◽  
Shengzu Duan ◽  
Jing Wang ◽  
Zhuo Chen ◽  
Tongqi Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Allyl Ether ◽  
Metal Catalyst ◽  
Metal Free ◽  
Allyl Ethers ◽  
Bond Forming ◽  
Allyl Halides ◽  
Synthetic Utility ◽  
Insight Into ◽  
Allyl Esters

AbstractAllylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

Transition Metal-free Single Step Approach for Arylated Pyrazolopyrimidinones and Quinazolinones Using Benzylamines/Benzylalcohols/Benzaldehydes

2017 ◽  
Vol 2 (17) ◽  
pp. 4963-4968 ◽  
Author(s):  
Abhinandan D. Hudwekar ◽  
G. Lakshma Reddy ◽  
Praveen K. Verma ◽  
Sorav Gupta ◽  
Ram A. Vishwakarma ◽  
...  
Keyword(s):  
Transition Metal ◽  
Single Step ◽  
Metal Free

Pyridine mediated transition-metal-free direct alkylation of anilines using alcohols via borrowing hydrogen conditions

2020 ◽  
Vol 56 (88) ◽  
pp. 13607-13610 ◽  
Author(s):  
Rajagopal Pothikumar ◽  
Venugopal T Bhat ◽  
Kayambu Namitharan
Keyword(s):  
Transition Metal ◽  
Traditional Approach ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Metal Free ◽  
Borrowing Hydrogen ◽  
Activation Of Alcohols ◽  
Catalyst Systems ◽  
Hydrogen Reactions

Herein, we report aza-aromatics based organic mediators as a readily accessible alternative to the traditional approach of using transition metal catalyst systems for the activation of alcohols in borrowing hydrogen reactions.

Transition-Metal-Free Catalysis for the Reductive ­Functionalization of CO2 with Amines

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 548-555 ◽  
Author(s):  
Liang-Nian He ◽  
Xiao-Fang Liu ◽  
Xiao-Ya Li ◽  
Chang Qiao
Keyword(s):  
Transition Metal ◽  
Energy Content ◽  
Bond Formation ◽  
Energy Storage Materials ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
Electron Reduction ◽  
Reduction Of Co2 ◽  
Hierarchical Reduction

Reductive functionalization of CO2 with amines and a reductant, which combines both reduction of CO2 and C–N bond formation in one pot to produce versatile chemicals and energy-storage materials such as formamides, aminals, and methylamines that are usually derived from petroleum feedstock, would be appealing and promising. Herein, we give a brief review on recent developments in the titled CO2 chemistry by employing transition-metal-free catalysis, which can be catalogued as below according to the diversified energy content of the products, that is formamides, aminals, and methylamines being consistent with 2-, 4-, and 6-electron reduction of CO2, respectively. Notably, hierarchical reduction of CO2 with amines to afford at least two products, for example, formamides and methylamines, could be realized with the same catalyst through tuning the hydrosilane type, reaction temperature, or CO2 pressure. Finally, the opportunities and challenges of the reductive functionalization of CO2 with amines are also highlighted.1 Introduction2 2-Electron Reduction of CO2 to Formamide3 6-Electron Reduction of CO2 to Methylamine4 4-Electron Reduction of CO2 to Aminal5 Hierarchical Reduction of CO2 with Amines6 Conclusion

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