Radical alkylation of C(sp3)–H bonds with diacyl peroxides under catalyst-free conditions

2019 ◽  
Vol 55 (98) ◽  
pp. 14813-14816 ◽  
Author(s):  
Hao Tian ◽  
Wentao Xu ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Alkyl Radical ◽  
Cross Coupling ◽  
Catalyst Free ◽  
Alkylation Reactions

Herein, we describe a protocol for alkylation reactions of C(sp3)–H bonds with diacyl peroxides by means of a process involving cross-coupling between an alkyl radical and an α-aminoalkyl radical.

An Oxidant- and Catalyst-Free Electrooxidative Cross-Coupling Approach to 3-Tetrahydroisoquinoline Substituted Coumarins

2021 ◽  
Author(s):  
Yanyan Kong ◽  
Jung Keun Kim ◽  
Yabo Li ◽  
Jianye Zhang ◽  
Mengmeng Huang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Fast Method ◽  
Catalyst Free ◽  
Dehydrogenative Coupling ◽  
Coupling Approach ◽  
Substituted Coumarins

A direct electrooxidative cross-dehydrogenative-coupling (CDC) reaction between N-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins has been developed. This protocol provides a green, mild and fast method to construct 3-tetrahydroisoquinoline substituted coumarins in the absence...

scholarly journals Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions

Synthesis ◽  
2020 ◽  
Vol 52 (08) ◽  
pp. 1279-1286
Author(s):  
Kamal K. Rajbongshi ◽  
Srinivas Ambala ◽  
Thavendran Govender ◽  
Hendrik G. Kruger ◽  
Per I. Arvidsson ◽  
...  
Keyword(s):  
Free Radical ◽  
Microwave Irradiation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aromatic Aldehydes ◽  
Efficient Catalyst ◽  
Radical Initiator ◽  
Catalyst Free ◽  
Broad Scope ◽  
Cross Coupling Reaction

An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in moderate to excellent yields (27 examples). This protocol proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

Catalyst-free phosphorylation of aryl halides with trialkyl phosphites through electrochemical reduction

2019 ◽  
Vol 55 (93) ◽  
pp. 14035-14038 ◽  
Author(s):  
Shuai Wang ◽  
Cheng Yang ◽  
Shuo Sun ◽  
Jianbo Wang
Keyword(s):  
Electrochemical Reduction ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Catalyst Free ◽  
Cross Coupling Reaction ◽  
Trialkyl Phosphites

A catalyst-free electrochemical cross-coupling reaction of aryl halides with trialkyl phosphites has been developed for the synthesis of aromatic phosphonates.

ChemInform Abstract: Catalyst-Free Cross-Coupling of N-Tosylhydrazones with Chromium(0) Fischer Carbene Complexes: A New Approach to Diarylethanone.

ChemInform ◽  
2016 ◽  
Vol 47 (13) ◽  
pp. no-no
Author(s):  
Fangdong Hu ◽  
Jinghui Yang ◽  
Ying Xia ◽  
Chen Ma ◽  
Haiping Xia ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Fischer Carbene Complexes ◽  
Carbene Complexes ◽  
New Approach ◽  
Fischer Carbene ◽  
Catalyst Free

scholarly journals Direct Cross-Coupling of Alcohols with O-Nucleophiles Mediated by N-Iodosuccinimide as a Precatalyst under Mild Reaction Conditions

Catalysts ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 858
Author(s):  
Njomza Ajvazi ◽  
Stojan Stavber
Keyword(s):  
Substrate Concentration ◽  
Cross Coupling ◽  
High Substrate Concentration ◽  
Reaction Conditions ◽  
One Pot ◽  
High Substrate ◽  
Direct Cross ◽  
Chemical Profiles ◽  
Alkylation Reactions

We report N-iodosuccinimide as the most efficient and selective precatalyst among the N-halosuccinimides for dehydrative O-alkylation reactions between various alcohols under high-substrate concentration reaction conditions. The protocol is non-metal, one-pot, selective, and easily scalable, with excellent yields; enhancing the green chemical profiles of these transformations.

scholarly journals Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

2021 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Zhanghua Gao
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Propargylic Alcohols ◽  
Catalyst Free ◽  
Cross Coupling Reaction ◽  
Reaction Proceeds ◽  
Acid Catalyzed

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

scholarly journals Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

2020 ◽  
Author(s):  
Megan Greaves ◽  
Thomas O. Ronson ◽  
Guy Lloyd-Jones ◽  
Feliu Maseras ◽  
Stephen Sproules ◽  
...  
Keyword(s):  
Alkyl Radical ◽  
Nickel Complex ◽  
Cross Coupling ◽  
Active Species ◽  
Alkyl Halides ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Alternative Pathways ◽  
Cross Coupling Reactions ◽  
Abstraction Reaction

The mechanism of the reactions between dppf-Ni0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(dppf)2], which undergoes a halide abstraction reaction with alkyl halides and rapidly captures the alkyl radical that is formed. The yields in prototypical nickel-catalysed Kumada cross-coupling reactions are shown to be improved by the addition of free phosphine ligands<br>

scholarly journals Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

2022 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Jia Chen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Propargylic Alcohols ◽  
Catalyst Free ◽  
Cross Coupling Reaction ◽  
Reaction Proceeds ◽  
Acid Catalyzed

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

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