Reaction of Trialkylboranes with Cyclic α-Diazo Ketones. A New Synthesis of α-Alkyl Cycloalkanones

1971 ◽  
Vol 49 (13) ◽  
pp. 2371-2373 ◽  
Author(s):  
John Hooz ◽  
Donald M. Gunn ◽  
Hiromichi Kono
Keyword(s):  
Cyclic Ketones ◽  
Efficient Procedure ◽  
Mild Conditions ◽  
New Synthesis ◽  
Reaction Proceeds ◽  
High Yields

An efficient procedure has been developed for the alkylation of cyclic ketones, based on the reaction of trialkylboranes with cyclic α-diazo ketones. The reaction proceeds under mild conditions, affords high yields of α-alkylated cycloalkanones, and circumvents certain difficulties inherent in previous alkylation methods.

scholarly journals Decarbonylation through Aldehydic C–H Bond Cleavage by a Cationic Iridium Catalyst

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 972-976 ◽  
Author(s):  
Tomohiko Shirai ◽  
Kazuki Sugimoto ◽  
Masaya Iwasaki ◽  
Ryuki Sumida ◽  
Harunori Fujita ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Catalyst System ◽  
Mild Conditions ◽  
Iridium Catalyst ◽  
Reaction Proceeds ◽  
High Yields

We report the decarbonylation of aldehydes through an aldehydic C–H bond cleavage catalyzed by a cationic iridium/bisphosphine catalyst. The reaction proceeds under relatively mild conditions to give the corresponding hydrocarbon products in moderate to high yields. In addition, this cationic iridium catalyst system can be applied to an asymmetric hydroacylation of ketones.

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 605-609 ◽  
Author(s):  
Fa-Guang Zhang ◽  
Jun-An Ma ◽  
Ning Lv ◽  
Yi-Qiang Tian
Keyword(s):  
Facile Synthesis ◽  
One Pot ◽  
Good Efficiency ◽  
Trifluoromethyl Ketones ◽  
Mild Conditions ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
High Yields ◽  
Unsaturated Trifluoromethyl Ketones

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Devaiah Vytla ◽  
Kumargurubaran Kaliyaperumal ◽  
Rajeswari Velayuthaperumal ◽  
Parinita Shaw ◽  
Raj Gautam ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Cyclization ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Reaction Proceeds ◽  
High Yields

AbstractA photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.

Facile Synthesis of β-Keto Sulfones Employing Fenton’s Reagent in DMSO

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 571-575 ◽  
Author(s):  
Vladimir Abaev ◽  
Olga Serdyuk ◽  
Petrakis Chalikidi ◽  
Maxim Uchuskin ◽  
Igor Trushkov
Keyword(s):  
Cost Effective ◽  
Fenton’S Reagent ◽  
Facile Synthesis ◽  
Fenton's Reagent ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields ◽  
Straightforward Approach

A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton’s reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.

Novel cyclization and reductive coupling of bicyclic olefins with alkyl propiolates catalyzed by nickel complexes

2002 ◽  
Vol 74 (1) ◽  
pp. 69-75 ◽  
Author(s):  
Dinesh Kumar Rayabarapu ◽  
Chien-Hong Cheng
Keyword(s):  
Nickel Complex ◽  
Room Temperature ◽  
Nickel Complexes ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields ◽  
Alkyl Propiolates

In this article, new metal-mediated cyclization and reductive coupling reactions of bicyclic olefins with alkynes are described. Oxabicyclic alkenes undergo cyclization with alkyl propiolates at 80 C catalyzed by nickel complexes to give benzocoumarin derivatives in high yields. The reaction of bicyclic alkenes (oxa- and azacyclic alkenes) with alkyl propiolates at room temperature in the presence of the same nickel complex gave 1,2-dihydro-napthelene derivatives in good-to-excellent yields. This reductive coupling reaction proceeds under very mild conditions in complete regio- and stereoselective fashion. A mechanism to account for the coumarin formation and the reductive coupling is proposed.

Ruthenium(II)-Catalyzed C–H Alkynylation of Heterocycles under Chelation Assistance

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 658-662 ◽  
Author(s):  
Congjun Liu ◽  
Yanping Liu ◽  
Feng Chang ◽  
Qiaojuan Jiang ◽  
Zhiwei Ma
Keyword(s):  
Functional Group ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields

An efficient ruthenium(II)-catalyzed, chelation-assisted C–H alkynylation of heterocycles is described using hypervalent iodine–alkyne as an alkynylating reagent. This reaction proceeds smoothly under mild conditions with high regioselectivity and good functional group tolerance, delivering the desired alkynylated indoles, thiophene, furan, and pyrrole in high yields.

A facile and efficient procedure for one-pot four-component synthesis of polysubstituted spiro pyrano[2,3-c]pyrazole and spiro 1,4-dihydropyridine catalyzed by a Dabco-based ionic liquid under mild conditions

2018 ◽  
Vol 42 (2) ◽  
pp. 1046-1051 ◽  
Author(s):  
Tong Liu ◽  
Yi-Huan Lai ◽  
Ya-Qin Yu ◽  
Da-Zhen Xu
Keyword(s):  
Ionic Liquid ◽  
One Pot ◽  
Efficient Procedure ◽  
Mild Conditions ◽  
High Yields

Spiro pyrano[2,3-c]pyrazoles and spiro 1,4-dihydropyridines were obtained in high yields from different amine components under Dabco-based ionic liquid catalysis.

An Efficient Direct Access to Carbamates from Alcohols and TosMIC Mediated by Iodine in DMSO

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2039-2042 ◽  
Author(s):  
Y. Prapurna ◽  
Naresh Pogaku ◽  
Palakodety Krishna
Keyword(s):  
Direct Access ◽  
New Approach ◽  
Mild Conditions ◽  
Rapid Construction ◽  
Practical Strategy ◽  
Dmso System ◽  
Reaction Proceeds ◽  
One Step ◽  
High Yields

A new approach for the synthesis of carbamates from alcohols and TosMIC promoted by iodine/DMSO system is reported. This method offers a one-step, direct and practical strategy for the rapid construction of carbamates under mild conditions. The reaction proceeds via sequential oxidation of isocyanide to isocyanate and nucleo­philic addition of alcohols to isocyanate to afford the carbamates in high yields.

scholarly journals Electrochemical multicomponent synthesis of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions

2021 ◽  
Author(s):  
Yan Wu ◽  
Jin-Yang Chen ◽  
Jing Ning ◽  
Xue Jiang ◽  
Jie Deng ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Raw Materials ◽  
Multicomponent Synthesis ◽  
Mild Conditions ◽  
Simple Protocol ◽  
High Yields

An electrochemical multicomponent reaction was established under catalyst-, chemical-oxidant-free and mild conditions, which provides an eco-friendly and simple protocol for constructing 4-selanylpyrazoles from easily available raw materials with high yields.

scholarly journals Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

2021 ◽  
Author(s):  
Travis DeLano ◽  
Sara Dibrell ◽  
Caitlin R. Lacker ◽  
Adam Pancoast ◽  
Kelsey Poremba ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Reaction Proceeds

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities....

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