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...

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.

Recent Advances in C–Br Bond Formation

Synlett ◽  
2021 ◽  
Author(s):  
Ying-Yeung Yeung ◽  
Jonathan Wong
Keyword(s):  
Organic Synthesis ◽  
Aromatic Compounds ◽  
Bond Formation ◽  
Cross Coupling ◽  
Catalytic Site ◽  
Atom Transfer ◽  
Bond Forming ◽  
Recent Advances ◽  
Catalytic Asymmetric ◽  
Site Selective

AbstractOrganobromine compounds are extremely useful in organic synthesis. In this perspective, a focused discussion on some recent advancements in C–Br bond-forming reactions is presented.1 Introduction2 Selected Recent Advances2.1 Catalytic Asymmetric Bromopolycyclization of Olefinic Substrates2.2 Catalytic Asymmetric Intermolecular Bromination2.3 Some New Catalysts and Reagents for Bromination2.4 Catalytic Site-Selective Bromination of Aromatic Compounds2.5 sp3 C–H Bromination via Atom Transfer/Cross-Coupling3 Outlook

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.

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.

Carboxylate Anions Accelerate Pyrrolidinopyridine (PPy)-Catalyzed Acylation: Catalytic Site-Selective Acylation of a Carbohydrate by in Situ Counteranion Exchange

2017 ◽  
Vol 19 (12) ◽  
pp. 3099-3102 ◽  
Author(s):  
Masanori Yanagi ◽  
Ayumi Imayoshi ◽  
Yoshihiro Ueda ◽  
Takumi Furuta ◽  
Takeo Kawabata
Keyword(s):  
Catalytic Site ◽  
Carboxylate Anions ◽  
Selective Acylation ◽  
Site Selective

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
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