scholarly journals Mechanistic studies on the metal-free decarboxylative coupling reaction for synthesis of propargylamines by NMR

ARKIVOC ◽  
2016 ◽  
Vol 2016 (5) ◽  
pp. 1-12
Author(s):  
Yongjun Lee ◽  
Kyungho Park ◽  
Han-Sung Kim ◽  
Jimin Kim ◽  
Young Ju Lee ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Decarboxylative Coupling

I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2018-2023 ◽  
Author(s):  
Xiang Fang ◽  
Xueyan Yang ◽  
Tongle Shao ◽  
Jun Zhou ◽  
Chen Jin ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Oxidation Pathway ◽  
Keto Esters ◽  
Oxidative Coupling Reaction

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

Electrochemical synthesis of enaminones via a decarboxylative coupling reaction

2019 ◽  
Vol 21 (14) ◽  
pp. 3796-3801 ◽  
Author(s):  
Xianqiang Kong ◽  
Yulong Liu ◽  
Long Lin ◽  
Qianjin Chen ◽  
Bo Xu
Keyword(s):  
Electrochemical Synthesis ◽  
Coupling Reaction ◽  
Metal Free ◽  
Redox Catalyst ◽  
Decarboxylative Coupling

Metal-free and oxidant-free n-Bu4NI as a redox catalyst and electrolyte.

Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Regioselective Alkylation ◽  
Decarboxylative Coupling ◽  
Aliphatic Carboxylic Acids

A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

Transition-metal free direct C–H functionalization of quinoxalin-2(1H)-ones with oxamic acids leading to 3-carbamoyl quinoxalin-2(1H)-ones

2020 ◽  
Vol 7 (2) ◽  
pp. 273-285 ◽  
Author(s):  
Jin-Wei Yuan ◽  
Jun-Liang Zhu ◽  
Hu-Lin Zhu ◽  
Fang Peng ◽  
Liang-Yu Yang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Free ◽  
Mild Conditions ◽  
Decarboxylative Coupling

A practical transition-metal free decarboxylative coupling reaction of oxamic acids with quinoxalin-2(1H)-ones has been developed under mild 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.

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 81-85
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Qiankun Fan ◽  
Yiyong Zhao ◽  
Huimin Wang
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Reductive Coupling ◽  
Mechanistic Studies ◽  
Dual Roles ◽  
Metal Free ◽  
Operational Simplicity

AbstractA tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO2·CH2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing–coupling pathway.

Metal-free electrochemical synthesis of α-ketoamides via decarboxylative coupling of α-keto acids with isocyanides and water

2021 ◽  
Author(s):  
Feng Zhao ◽  
Na Meng ◽  
Ting Sun ◽  
Jiangwei Wen ◽  
Xiaohui Zhao ◽  
...  
Keyword(s):  
Electrochemical Synthesis ◽  
Coupling Reaction ◽  
Environmentally Benign ◽  
Metal Free ◽  
Keto Acids ◽  
Decarboxylative Coupling

A mild and environmentally benign electrochemical strategy has been developed for the synthesis of α-ketoamides via a decarboxylative coupling reaction of α-keto acids with isocyanides and water. The present reaction...

Synthesis of Acetamides from Aryl Amines and Acetonitrile by Diazotization under Metal-Free Conditions

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2169-2172 ◽  
Author(s):  
Yao-Fu Zeng ◽  
Yi-Na Li ◽  
Na-Na Zhang ◽  
Huan Kang ◽  
Pan Duan ◽  
...  
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Wide Range ◽  
Aryl Amines

An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

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