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...

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Yan-Wei Zhao ◽  
Shun-Yi Wang ◽  
Xin-Yu Liu ◽  
Tian Jiang ◽  
Weidong Rao
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Radical Cyclization ◽  
Transition Metal Catalysis ◽  
Insertion Reaction ◽  
Metal Catalysis ◽  
Metal Free ◽  
Benzothiazole Derivatives

AbstractA synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines

Synlett ◽  
2020 ◽  
Author(s):  
Lei Jiao ◽  
Fei-Yu Zhou
Keyword(s):  
Transition Metal ◽  
Structural Motif ◽  
Metal Exchange ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Metal Free ◽  
Radical Coupling ◽  
In Situ Activation ◽  
Recent Developments

AbstractPyridine is an important structural motif that is prevalent in natural products, drugs, and materials. Methods that functionalize and derivatize pyridines have gained significant attention. Recently, a large number of transition-metal-free reactions have been developed. In this review, we provide a brief summary of recent advances in transition-metal-free functionalization and derivatization reactions of pyridines, categorized according to their reaction modes.1 Introduction2 Metalated Pyridines as Nucleophiles2.1 Deprotonation2.2 Halogen–Metal exchange3 Activated Pyridines as Electrophiles3.1 Asymmetric 2-Allylation by Chiral Phosphite Catalysis3.2 Activation of Pyridines by a Bifunctional Activating Group3.3 Alkylation of Pyridines by 1,2-Migration3.4 Alkylation of Pyridines by [3+2] Addition3.5 Pyridine Derivatization by Catalytic In Situ Activation Strategies3.6 Reactions via Heterocyclic Phosphonium Salts4 Radical Reactions for Pyridine Functionalization4.1 Pyridine Functionalization through Radical Addition Reactions4.2 Pyridine Functionalization through Radical–Radical Coupling Reactions5 Derivatization of Pyridines through the Formation of Meisenheimer-Type Pyridyl Anions6 Conclusion

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.

ChemInform Abstract: In situ Generation of PhI+CF3and Transition-Metal-Free Oxidative sp2C-H Trifluoromethylation.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Cong Xu ◽  
Jingxin Liu ◽  
Wenbo Ming ◽  
Yingjie Liu ◽  
Jun Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
In Situ Generation

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.

nBu4NOTf-promoted radical self-hydrogen transferring isomerization under transition metal-free conditions

2018 ◽  
Vol 5 (7) ◽  
pp. 1213-1216 ◽  
Author(s):  
Hong-Xing Zheng ◽  
Chuan-Zhi Yao ◽  
Jian-Ping Qu ◽  
Yan-Biao Kang
Keyword(s):  
Transition Metal ◽  
Metal Free

We report the first allylic isomerization of alcohols catalyzed by nBu4NOTf generated in situ from tetrabutylammonium triflate and potassium tert-butoxide.

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.

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