Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines

2019 ◽  
Vol 17 (32) ◽  
pp. 7438-7441 ◽  
Author(s):  
Ju-You Lu ◽  
Bo Zhao ◽  
Yongmei Du ◽  
Jianxin Yang ◽  
Jian Lu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Metal Free

An efficient C(cage)–heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines under transition-metal-free conditions. The process utilizes readily available carboranyllithium nucleophile, and exhibits a broad substrate scope.

scholarly journals Water promoted allylic nucleophilic substitution reactions of (E)-1,3 diphenylallyl acetate

2018 ◽  
Vol 20 (2) ◽  
pp. 425-430 ◽  
Author(s):  
Seema A. Ghorpade ◽  
Dinesh N. Sawant ◽  
Arwa Makki ◽  
Nagaiyan Sekar ◽  
Jörg Eppinger
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Allylic Alkylation ◽  
Substitution Reactions ◽  
Allylic Amination ◽  
Metal Free ◽  
Nucleophilic Substitution Reactions ◽  
Water Based

A transition metal free, reagent free, only water based, greener protocol for the allylic alkylation, allylic amination, and O-allylation of (E)-1,3-diphenylallyl acetate is described.

Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride

2018 ◽  
Vol 16 (41) ◽  
pp. 7564-7567 ◽  
Author(s):  
Yibiao Li ◽  
Shuo Huang ◽  
Chunshu Liao ◽  
Yan Shao ◽  
Lu Chen
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Efficient Method ◽  
Free Access ◽  
Metal Free ◽  
Catalyst Free ◽  
Hydrolysis Of

Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed.

Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

2015 ◽  
Vol 13 (13) ◽  
pp. 3982-3987 ◽  
Author(s):  
Jie Zhang ◽  
Ying Shao ◽  
Yaxiong Wang ◽  
Huihuang Li ◽  
Dongmei Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Amino Acid Esters ◽  
Dimethyl Malonate ◽  
Metal Free ◽  
New Strategy ◽  
Efficient Construction ◽  
Acid Esters

A new strategy has been developed for the synthesis of α-amino acid esters via a tandem hydrolysis/decarboxylation/nucleophilic substitution using TBAI/TBHP.

Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution

2019 ◽  
Vol 55 (87) ◽  
pp. 13124-13127 ◽  
Author(s):  
Zhicheng Fu ◽  
Simin Sun ◽  
Anjian Yang ◽  
Fang Sun ◽  
Jiaxi Xu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Michael Addition ◽  
Nucleophilic Addition ◽  
Free Access ◽  
Metal Free

3,4-Dihydro-1,2-oxaphosphinine 2-oxides are synthesized through tandem intermolecular nucleophilic addition and cyclization of phosphonochloridates and enones in the presence of base.

(Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K

2019 ◽  
Vol 17 (31) ◽  
pp. 7315-7319 ◽  
Author(s):  
Xianglin Luo ◽  
Yibiao Li ◽  
Xiuwen Chen ◽  
Zhiyan Song ◽  
Junyi Liang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Thiyl Radical ◽  
Intramolecular Cycloaddition ◽  
Free Condition ◽  
Metal Free ◽  
Novel Method

This protocol provides a novel method for the synthesis of (Z)-tetrahydrothiophene derivatives through the formation of C–S bonds under transition-metal-free condition using thiyl radical intramolecular cycloaddition cascade strategy.

Synthesis of (benzenesulfonyl)difluoromethyl thioethers from ((difluoromethyl)sulfonyl)benzene and organothiocyanates generated in situ

2021 ◽  
Author(s):  
Cheng Wu ◽  
Xiao Shen ◽  
Jian-Jun Dai ◽  
Jun Xu ◽  
Hua-Jian Xu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Metal Free

Easily available aryl and alkyl thiocyanates were converted into the corresponding (benzenesulfonyl)difluoromethyl thioethers via direct nucleophilic substitution of ((difluoromethyl)-sulfonyl)benzene under transition metal free conditions. Combined with various thiocyanation methods, this...

scholarly journals Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

2018 ◽  
Vol 14 ◽  
pp. 2618-2626 ◽  
Author(s):  
Lidia A Smyshliaeva ◽  
Mikhail V Varaksin ◽  
Pavel A Slepukhin ◽  
Oleg N Chupakhin ◽  
Valery N Charushin
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Advanced Materials ◽  
Synthetic Approach ◽  
Nucleophilic Substitution Of Hydrogen ◽  
One Pot ◽  
Metal Free

The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (SN H) in non-aromatic azaheterocycles, affords novel imidazolyl-modified carboranes of two types (N-oxides and their deoxygenative analogues), which are particularly of interest in the design of advanced materials.

Transition-Metal-Free С–С Coupling of 5,7-Dihydroxybenzopyrones with Quinoxalones and Pteridinones

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2423-2431 ◽  
Author(s):  
Igor Khalymbadzha ◽  
Ramil Fatykhov ◽  
Oleg Chupakhin ◽  
Valery Charushin ◽  
Tatiana Tseitler ◽  
...  
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Coupling Reaction ◽  
Environmentally Benign ◽  
Pyrazine Ring ◽  
Metal Free ◽  
Mild Conditions ◽  
Hybrid Compounds ◽  
Direct Incorporation

A new synthetic protocol for nucleophilic substitution of hydrogen­ in quinoxalones and pteridinones by the action of 5,7-di­hydroxycoumarins and related m-dihydroxybenzene compounds has been developed. The C–C coupling reaction proved to proceed smoothly under rather mild conditions, thus giving the corresponding C–H functionalized products in good yields. The advantages of this environmentally benign protocol are high regio- and chemoselectivity, and an easy workup procedure. Direct incorporation of the coumarin moiety into the pyrazine ring in pteridines or quinoxalines provides a short pathway to pyrazine-coumarin hybrid compounds.

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