Transition-Metal-Free Synthesis of Trifluoromethylated Furans via a Bu3P-Mediated Tandem Acylation–Wittig Reaction

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2035-2038
Author(s):  
Wei Zhou ◽  
Maizhan Li
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Nucleophilic Addition ◽  
Wittig Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
Highly Efficient ◽  
Intramolecular Wittig Reaction ◽  
High Yields

AbstractA highly efficient nucleophilic addition–O-acylation–intramolecular Wittig reaction of β-trifluoromethyl α,β-enones is disclosed. This strategy features mild reaction conditions and provides a practical transition-metal-free method to a set of biologically significant trifluoromethylated furans in high yields with diverse functional groups.

A Convenient Strategy for Remote C–H Bond Halogenation of 8-Aminoquinolines in the C5 Position

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1840-1844 ◽  
Author(s):  
Xiang-Xiang Chen ◽  
Jia-Xin Wang ◽  
Jiang-Tao Ren ◽  
Hu Xie ◽  
Yanxia Zhao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Metal Free ◽  
Highly Efficient

A highly efficient and convenient strategy has been developed for remote C–H bond halogenation of 8-aminoquinolines in good to excellent yields under transition-metal-free conditions. The reaction tolerates a variety of functional groups and can potentially be scaled up.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2076-2080 ◽  
Author(s):  
Wen-Ting Wei ◽  
Zhiyong Guo ◽  
Guodong Zhou ◽  
Xu-Dong Xu ◽  
Gan-Ping Chen
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Metal Free ◽  
Radical Coupling ◽  
Radical Coupling Reaction ◽  
High Yields

An efficient and practical transition-metal-free radical ­coupling reaction of sulfonyl hydrazides mediated by NIS/K2S2O8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S–S bonds.

A Highly Efficient Copper(II)-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with 2-Arylimidazo[1,2-a]pyridines

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2775-2783 ◽  
Author(s):  
Zhi-Qiang Zhu ◽  
Zhang-Gao Le ◽  
Li-Jin Xiao ◽  
Ying Chen ◽  
Zong-Bo Xie ◽  
...  
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Coupling Reaction ◽  
Amino Acid Esters ◽  
Synthetic Method ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
High Yields ◽  
Acid Esters

A rapid and highly efficient copper(II)-catalyzed cross-dehydrogenative coupling (CDC) reaction of N-arylglycine esters with imidazo[1,2-a]pyridines has been described. A broad range of N-arylglycine esters underwent the CDC reaction smoothly with 2-arylimidazo[1,2-a]pyridines to give α-substituted α-amino acid esters in excellent yields. This synthetic method has the advantages of high yields, good functional groups compatibility, simple operation, and mild reaction conditions. A possible mechanism for the CDC reaction is also proposed. The use of a copper salt as the catalyst and air as the terminal oxidant makes this transformation sustainable and practical.

Deuterative cyclization of sulfanyl 1,6-diynes: complete and monodeuteration of functional groups on heterocycles

2015 ◽  
Vol 2 (3) ◽  
pp. 201-205 ◽  
Author(s):  
Yukiteru Ito ◽  
Mitsuhiro Yoshimatsu
Keyword(s):  
Transition Metal ◽  
Exchange Reaction ◽  
Functional Groups ◽  
Reductive Cyclization ◽  
Metal Free ◽  
Sodium Borodeuteride

Regioselective H/D exchange reaction of functional groups on heterocycles proceeded via a transition metal-free reductive cyclization of sulfanyl 1,6-diynes using sodium borodeuteride/ethanol-D1.

Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions

2018 ◽  
Vol 24 (1) ◽  
pp. 23-26
Author(s):  
Zheng Li ◽  
Wenli Song ◽  
Jiaojiao He ◽  
Yan Du ◽  
Jingya Yang
Keyword(s):  
Efficient Method ◽  
Michael Addition ◽  
Nucleophilic Addition ◽  
Tandem Reactions ◽  
Reaction Conditions ◽  
High Yields ◽  
Work Up

Abstract An efficient method for the synthesis of the title compounds by reactions of divinyl ketones with thiourea is described. This protocol has the advantages of high yields, mild reaction conditions and simple work-up procedure.

One-pot transition-metal free transamidation to sterically hindered amides

2018 ◽  
Vol 5 (20) ◽  
pp. 2950-2954 ◽  
Author(s):  
Weijie Guo ◽  
Jingjun Huang ◽  
Hongxiang Wu ◽  
Tingting Liu ◽  
Zhongfeng Luo ◽  
...  
Keyword(s):  
Transition Metal ◽  
Good Yield ◽  
One Pot ◽  
Metal Free ◽  
Highly Efficient ◽  
Sterically Hindered

A highly efficient one-pot transamidation of primary amides has been developed under transition-metal free conditions, generating a variety of amides including hindered amides in good yield (up to 86%) catalyzed by CsF.

Transition-metal-free arylation of benzoxazoles with aryl nitriles

2018 ◽  
Vol 5 (11) ◽  
pp. 1811-1814 ◽  
Author(s):  
Aizhen Wu ◽  
Quan Chen ◽  
Wei Liu ◽  
Lijun You ◽  
Yifan Fu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Reaction Conditions ◽  
Metal Free ◽  
Simple Reaction ◽  
Aryl Nitriles

Transition-metal-free arylation of benzoxazoles with aryl nitriles has been developed to afford important 2-aryl benzoxazoles under simple reaction conditions.

Synthesis of 2-Chromanone-fused [3.2.0] Bicycles through a Phosphine-mediated Tandem [3+2] Cyclization/Intramolecular Wittig Reaction

2021 ◽  
Author(s):  
Junfeng Fu ◽  
Ingrid Rakielle Tsapy Takia ◽  
Peng Chen ◽  
Wei Liu ◽  
Chengjun Jiang ◽  
...  
Keyword(s):  
Wittig Reaction ◽  
High Efficiency ◽  
Intramolecular Wittig Reaction ◽  
Tandem Process ◽  
High Yields

A phosphine-mediated tandem [3+2] cyclization/intramolecular Wittig reaction of 3-aroylcoumarin with alkynone is described. The high efficiency of tandem process allows the synthesis of 2-chromanone-fused bicyclo[3.2.0]heptenones in moderate to high yields...

scholarly journals Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 459 ◽  
Author(s):  
Hengzhao Li ◽  
Zemin Lai ◽  
Adila Adijiang ◽  
Hongye Zhao ◽  
Jie An
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transfer Reaction ◽  
Bond Cleavage ◽  
Electron Transfer Reaction ◽  
Amide Bond ◽  
Single Electron Transfer ◽  
Reaction Conditions ◽  
Metal Free ◽  
Single Electron Transfer Reaction

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.

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