Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives

2013 ◽  
Vol 78 (21) ◽  
pp. 10642-10650 ◽  
Author(s):  
Toshimitsu Moriya ◽  
Shinichiro Yoneda ◽  
Keita Kawana ◽  
Reiko Ikeda ◽  
Takeo Konakahara ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
One Pot ◽  
Alkyl Bromides

ChemInform Abstract: Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives.

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
Toshimitsu Moriya ◽  
Shinichiro Yoneda ◽  
Keita Kawana ◽  
Reiko Ikeda ◽  
Takeo Konakahara ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
One Pot ◽  
Alkyl Bromides

Use of Ethyl (Benzothiazol-2-ylsulfonyl)acetate for Malonic Ester-type Syntheses of Carboxylic Acids and Esters

2014 ◽  
Vol 67 (9) ◽  
pp. 1222 ◽  
Author(s):  
Waleed M. Hussein ◽  
Ross P. McGeary
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
Malonic Ester ◽  
One Pot ◽  
Dichloromethane Solution ◽  
Mild Conditions ◽  
Acetic Acids

A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.

scholarly journals Direct C(sp2)–H alkylation of unactivated arenes enabled by photoinduced Pd catalysis

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Daeun Kim ◽  
Geun Seok Lee ◽  
Dongwook Kim ◽  
Soon Hyeok Hong
Keyword(s):  
Functional Group ◽  
Alkyl Halide ◽  
Alkyl Halides ◽  
Biologically Active ◽  
One Pot ◽  
Bond Forming ◽  
Alkyl Groups ◽  
Alkyl Bromides ◽  
Reaction Proceeds ◽  
Alkylation Reactions

AbstractDespite the fundamental importance of efficient and selective synthesis of widely useful alkylarenes, the direct catalytic C(sp2)–H alkylation of unactivated arenes with a readily available alkyl halide remains elusive. Here, we report the catalytic C(sp2)–H alkylation reactions of unactivated arenes with alkyl bromides via visible-light induced Pd catalysis. The reaction proceeds smoothly under mild conditions without any skeletal rearrangement of the alkyl groups. The direct syntheses of structurally diverse linear and branched alkylarenes, including the late-stage phenylation of biologically active molecules and an orthogonal one-pot sequential Pd-catalyzed C–C bond-forming reaction, are achieved with exclusive chemoselectivity and exceptional functional group tolerance. Comprehensive mechanistic investigations through a combination of experimental and computational methods reveal a distinguishable Pd(0)/Pd(I) redox catalytic cycle and the origin of the counter-intuitive reactivity differences among alkyl halides.

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides with Alkyl Carboxylic Acids

2021 ◽  
Author(s):  
Ke-Jin Jiao ◽  
Cong Ma ◽  
Dong Liu ◽  
Hui Qiu ◽  
Bin Cheng ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Undivided Cell ◽  
Alkyl Bromides ◽  
Direct Acylation

A highly regioselective Ni-catalyzed electrochemical (undivided cell) reductive relay cross-coupling between alkyl carbox-ylic acids and alkyl bromides has been developed. This strategy allows the direct acylation of benzylic C(sp3)–H bonds...

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

scholarly journals Dehalogenation of functionalized alkyl halides in water at room temperature

2015 ◽  
Vol 17 (2) ◽  
pp. 893-897 ◽  
Author(s):  
Nicholas A. Isley ◽  
Matt S. Hageman ◽  
Bruce H. Lipshutz
Keyword(s):  
Room Temperature ◽  
Alkyl Halides ◽  
Alkyl Bromides ◽  
Green Conditions

Alkyl bromides and chlorides can be reduced to the corresponding hydrocarbons utilizing zinc in the presence of an amine additive under very mild, green conditions.

Mild one-pot conversion of carboxylic acids to amides or esters with Ph3P/trichloroisocyanuric acid

2005 ◽  
Vol 46 (35) ◽  
pp. 5945-5947 ◽  
Author(s):  
Rogério da C. Rodrigues ◽  
Igor M.A. Barros ◽  
Edson L.S. Lima
Keyword(s):  
Carboxylic Acids ◽  
One Pot ◽  
Trichloroisocyanuric Acid
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