Site-Selective and Metal-Free Aliphatic CH Oxidation Enabled Synthesis of [5,24,25-D3]-(25S)-Δ7-Dafachronic acid

2015 ◽  
Vol 21 (14) ◽  
pp. 5345-5349 ◽  
Author(s):  
Weilong Liu ◽  
Xiangke Li ◽  
Jie Chen ◽  
Tiemei Li ◽  
Mengqiu Dong ◽  
...  
Keyword(s):  
Metal Free ◽  
Dafachronic Acid ◽  
Site Selective

Metal-free amino-controlled electrochemical intramolecular C–O and C–N couplings by site-selective activation of aryl C–N and C–O bonds

2021 ◽  
Author(s):  
Mu-Jia Luo ◽  
Gui-Fen Lv ◽  
Yang Li ◽  
Jin-Heng Li
Keyword(s):  
Free Amino ◽  
Selective Activation ◽  
Metal Free ◽  
Site Selective

Metal-free amino-assisted electrochemical intramolecular C–O or C–N couplings of amino-2-(2-aminoaryl)phenols are described.

Transition‐Metal‐Free Hypervalent Iodine(III) Reagent‐Promoted Site‐Selective Solid‐Phase Synthesis of Mononitroarylamines

2018 ◽  
Vol 3 (45) ◽  
pp. 12946-12950 ◽  
Author(s):  
Delie An ◽  
Wenkang Song ◽  
Zhihong Peng ◽  
Yingjun Zhang ◽  
Wanrong Dong
Keyword(s):  
Transition Metal ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hypervalent Iodine ◽  
Phase Synthesis ◽  
Metal Free ◽  
Site Selective

scholarly journals Metal-free site-selective C–H cyanoalkylation of 8-aminoquinoline and aniline-derived amides with azobisisobutyronitrile

RSC Advances ◽  
2021 ◽  
Vol 11 (49) ◽  
pp. 30719-30724
Author(s):  
Mengfei Zhao ◽  
Zengxin Qin ◽  
Kaixin Zhang ◽  
Jizhen Li
Keyword(s):  
Metal Free ◽  
Good Substrate ◽  
Substrate Tolerance ◽  
Site Selective

An efficient metal-free cyanoalkylation of 8-aminoquinoline and aniline-derived amides was achieved in the presence of K2S2O8. The method showed good substrate tolerance and also suitable for bromination and dimerization reactions.

B(C6F5)3-catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

2021 ◽  
Author(s):  
Yunbo Zhao ◽  
Dipendu Mandal ◽  
Jing Guo ◽  
Yile Wu ◽  
Douglas W Stephan
Keyword(s):  
Catalytic Site ◽  
Metal Free ◽  
Site Selective

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of...

Sodium persulfate-promoted site-selective synthesis of mononitroarylamines under transition-metal-free conditions

Tetrahedron ◽  
2019 ◽  
Vol 75 (9) ◽  
pp. 1157-1165
Author(s):  
De-Xun Xie ◽  
Hui-Juan Yu ◽  
Hui Liu ◽  
Wei-Cai Xue ◽  
Yuan-Shou Qin ◽  
...  
Keyword(s):  
Transition Metal ◽  
Selective Synthesis ◽  
Sodium Persulfate ◽  
Metal Free ◽  
Site Selective

scholarly journals Site-selective remote C(sp3)–H heteroarylation of amides via organic photoredox catalysis

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Hui Chen ◽  
Wenjing Fan ◽  
Xiang-Ai Yuan ◽  
Shouyun Yu
Keyword(s):  
Hydrogen Atom ◽  
Room Temperature ◽  
Ph Value ◽  
Metal Free ◽  
Selective Functionalization ◽  
Site Selectivity ◽  
Hydrogen Atom Transfers ◽  
Site Selective ◽  
Neutral Conditions ◽  
Potential Complement

Abstract Radical translocation processes triggered by nitrogen-centered radicals (NCRs), such as 1,5-hydrogen atom transfers (1,5-HAT), demonstrated by the well-established Hofmann-Löffler-Freytag (HLF) reaction, provide an attractive approach for the controllable and selective functionalization of remote inert C(sp3)–H bonds. Here we report an amidyl radical-triggered site-selective remote C(sp3)–H heteroarylation of amides under organic photoredox conditions. This approach provides a mild and highly regioselective reaction affording remote C(sp3)–H heteroarylated amides at room temperature under transition-metal free, weakly basic, and redox-neutral conditions. Non-prefunctionalized heteroarenes, such as purines, thiazolopyridines, benzoxazole, benzothiazoles, benzothiophene, benzofuran, thiazoles and quinoxalines, can be alkylated directly. Sequential and orthogonal C–H functionalization of different heteroarenes by taking advantage pH value or polarity of radicals has also been achieved. DFT calculations explain and can predict the site-selectivity and reactivity of this reaction. This strategy expands the scope of the Minisci reaction and serves as its alternative and potential complement.

scholarly journals Correction to: Site-selective and metal-free C–H nitration of biologically relevant N-heterocycles

2021 ◽  
Author(s):  
Junghyea Moon ◽  
Hyun Ku Ji ◽  
Nayoung Ko ◽  
Harin Oh ◽  
Min Seo Park ◽  
...  
Keyword(s):  
Biologically Relevant ◽  
Metal Free ◽  
Site Selective

scholarly journals A general arene C–H functionalization strategy via electron donor-acceptor complex photoactivation

2021 ◽  
Author(s):  
Abhishek Dewanji ◽  
Leendert van Dalsen ◽  
James Rossi-Ashton ◽  
Eloise Gasson ◽  
Giacomo Crisenza ◽  
...  
Keyword(s):  
Electronic Properties ◽  
Electron Donor ◽  
Late Stage ◽  
Aryl Halide ◽  
Aryl Radical ◽  
Sulfonium Salt ◽  
Radical Species ◽  
Metal Free ◽  
Donor Acceptor ◽  
Site Selective

The photoactivation of electron donor-acceptor (EDA) complexes has emerged as a sustainable, selective and versa-tile strategy for the generation of radical species. However, when it comes to aryl radical formation, this strategy remains hamstrung by the electronic properties of the aromatic radical precursors and electron-deficient aryl halide acceptors are required. This has prevented the implementation of a general synthetic platform for aryl radical for-mation. Our study introduces triarylsulfonium salts as acceptors in photoactive EDA-complexes, used in combina-tion with catalytic amounts of newly-designed amine donors. The sulfonium salt label renders inconsequential the electronic features of the aryl radical precursor and, more importantly, it is installed regioselectively in native aro-matic compounds by C–H sulfenylation. Using this general, site-selective aromatic C–H functionalization approach, we have developed metal-free protocols for the alkylation and cyanation of arenes, and showcased their application in both the synthesis and the late-stage modification of pharmaceuticals and agrochemicals.

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