Unorthodox cascade reaction of arynes and N-nitrosamides leading to indazole scaffolds?
Chemical Communications Pub Date: 2021-12-20 DOI: 10.1039/D1CC05655G
Abstract
An unusual cascade annulation of arynes with N-alkyl-N-nitrosamides is developed by leveraging aryne σ-insertion and C(sp3)–H bond functionalization strategies under transition-metal-free conditions at ambient temperature, offering functionalized indazoles in high yields and regioselectivity. The protocol is scalable and exhibits a broad substrate scope. The reaction mechanism is also studied with DFT calculations.
Recommended Literature
- [1] Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon? Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng PuChem. Commun., 2019,55, 3963-3966 10.1039/C9CC01213C
- [2] Evolution of dealloying induced strain in nanoporous gold crystals? Ross Harder,David C. Dunand,Ian McNultyNanoscale, 2017,9, 5686-5693 10.1039/C6NR09635B
- [3] Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination? Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. SharadaChem. Commun., 2022,58, 1406-1409 10.1039/D1CC06097J
- [4] Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study? Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander OrlovCatal. Sci. Technol., 2015,5, 2059-2064 10.1039/C4CY01563K
- [5] Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation Matthew J. Gaunt,Jinquan Yu,Jonathan B. SpencerChem. Commun., 2001, 1844-1845 10.1039/B103066N
- [6] Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond? Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin LiuChem. Commun., 2018,54, 10092-10095 10.1039/C8CC05410J
- [7] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [8] Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications? Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping XieNanoscale Adv., 2020,2, 3921-3932 10.1039/D0NA00381F
- [9] Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita 10.1002/rcm.9494
- [10] Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration? Ziyang Deng,Changwei Chen,Sunliang CuiRSC Adv., 2016,6, 93753-93755 10.1039/C6RA20007A
Journal Name:Chemical Communications
research_products
-
CAS no.: 89640-58-4