Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

2020 ◽  
Vol 56 (29) ◽  
pp. 4067-4069 ◽  
Author(s):  
Ya-Nan Wu ◽  
Ming-Chen Fu ◽  
Rui Shang ◽  
Yao Fu
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Aromatic Carboxylic Acids ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Lithium Formate

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1572-1577 ◽  
Author(s):  
Hua Fu ◽  
Min Jiang ◽  
Haijun Yang ◽  
Yunhe Jin ◽  
Lunyu Ou
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Functional Groups ◽  
High Efficiency ◽  
Aromatic Carboxylic Acids ◽  
Mild Conditions ◽  
Aryl Iodides

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4303-4308 ◽  
Author(s):  
Dong Li ◽  
Chuancheng Zhang ◽  
Qiang Yue ◽  
Zhen Xiao ◽  
Xianglan Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Electrophilic Amination ◽  
Mild Conditions

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

scholarly journals Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Purui Zheng ◽  
Pan Zhou ◽  
Dong Wang ◽  
Wenhao Xu ◽  
Hepan Wang ◽  
...  
Keyword(s):  
Visible Light ◽  
Ambient Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Strong Base ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Boronic Esters

AbstractThe flourishing Ni/photoredox-catalyzed asymmetric couplings typically rely on redox-neutral reactions. In this work, we report a reductive cross-coupling of aryl iodides and α-chloroboranes under a dual catalytic regime to further enrich the metallaphotoredox chemistry. This approach proceeds under mild conditions (visible light, ambient temperature, no strong base) to access the versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities.

KI-catalyzed α-acyloxylation of acetone with carboxylic acids

2016 ◽  
Vol 14 (25) ◽  
pp. 5936-5939 ◽  
Author(s):  
Ya-Dong Wu ◽  
Bei Huang ◽  
Yue-Xin Zhang ◽  
Xiao-Xu Wang ◽  
Jian-Jun Dai ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Present Method ◽  
Functional Group ◽  
Reaction Conditions ◽  
Aromatic Carboxylic Acids

A KI catalyzed reaction of acetone with aromatic carboxylic acids is achieved, leading to α-acyloxycarbonyl compounds in good to excellent yields under mild reaction conditions. The present method exhibits good functional-group compatibility.

scholarly journals Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks

2019 ◽  
Author(s):  
Joseph Derosa ◽  
Taeho Kang ◽  
Van Tran ◽  
Steven Wisniewski ◽  
Malkanthi Karunananda ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Cross Coupling ◽  
Building Blocks ◽  
Step Count ◽  
Bioactive Molecules ◽  
Aryl Iodides ◽  
Boronic Esters ◽  
Synthetic Utility

A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate functional group.

scholarly journals Selective Esterification of Nonconjugated Carboxylic Acids in the Presence of Conjugated or Aromatic Carboxylic Acids under Mild Conditions

1999 ◽  
Vol 23 (6) ◽  
pp. 378-379
Author(s):  
Ramesh C. Anand ◽  
Vimal ◽  
Archana Milhotra
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Aromatic Carboxylic Acids ◽  
Selective Esterification ◽  
Amberlyst 15 ◽  
Mild Conditions

Nonconjugated carboxylic acids are selectively esterified in good yields in the presence of conjugated or aromatic carboxylic acids by stirring over Amberlyst-15 in alcohol at room temperature.

Iridium-catalyzed regio- and enantioselective allylic esterification of secondary allylic alcohols with carboxylic acids

2021 ◽  
Author(s):  
Shengbiao Tang ◽  
Peng Zhang ◽  
Changkai Wang ◽  
Ying Shao ◽  
Jiangtao Sun
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Allylic Alcohols ◽  
Mild Conditions

We report herein an iridium-catalyzed asymmetric allylic esterification of racemic secondary allylic alcohols with carboxylic acids under mild conditions with broad functional group tolerance, exhibiting excellent regio- (b/l > 19 : 1) and enantioselectivity (up to >99% ee).

Construction of Esters through Sulfuryl Fluoride (SO2F2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3901-3907 ◽  
Author(s):  
Shi-Meng Wang ◽  
Njud S. Alharbi ◽  
Hua-Li Qin
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
High Efficiency ◽  
Sulfuryl Fluoride ◽  
Mild Conditions ◽  
High Yields

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO2F2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

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