Diiodine–Triethylsilane System: Reduction of N-Sulfonyl Aldimines to N-Alkylsulfonamides

Synlett ◽  
2020 ◽  
Author(s):  
Jin Jiang ◽  
Lili Xiao ◽  
Yu-Long Li
Keyword(s):  
Practical Method ◽  
Molecular Iodine ◽  
Reaction Conditions ◽  
System Reduction

AbstractBecause molecular iodine and hydrosilanes are stable to both air and moisture, reactions using these reagents are easy to operate and require mild reaction conditions. Molecular iodine and a hydrosilane were used to reduce N-sulfonyl aldimines to the corresponding N-alkylsulfonamides. This transformation is a practical method for the synthesis of N-alkylsulfonamides.

Molecular-Iodine-Promoted Synthesis of Dihydrobenzofuran-3,3-dicarbonitriles through a Novel Rearrangement

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 293-298
Author(s):  
Nagaraju Medishetti ◽  
Ashok Kale ◽  
Jagadeesh Nanubolu ◽  
Krishnaiah Atmakur
Keyword(s):  
Molecular Iodine ◽  
Basic Medium ◽  
Reaction Conditions ◽  
Simple Reaction

The title compounds were synthesized from 5,5-dimethyl­cyclohexane-1,3-dione, benzaldehyde, and malononitrile promoted by molecular iodine in basic medium via 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, by a novel protocol. The protocol involves a novel rearrangement in which the 4H-chromene fragment dissociates to a cyclopropane moiety and rearranges to the five-membered compound 6,6-dimethyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran-3,3(2H)-dicarbonitrile. Simple reaction conditions, excellent yields, and high compatibility are the advantages of this protocol.

scholarly journals Morpholin-2-one Derivatives via Intramolecular Acid-Catalyzed Hydroamination

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1643-1648 ◽  
Author(s):  
David Knight ◽  
Thomas Wirth ◽  
Abdul Hadi Aldmairi
Keyword(s):  
Amino Acids ◽  
Catalytic Amount ◽  
Practical Method ◽  
Trifluoromethanesulfonic Acid ◽  
Reaction Conditions ◽  
Available N ◽  
Metal Free ◽  
Acid Catalyzed

Substituted morpholin-2-one derivatives were readily obtained in two steps starting from commercially available N-protected amino acids. In a metal-free and practical method, a catalytic amount of trifluoromethanesulfonic acid was sufficient to generate morpholinones under mild reaction conditions in an intramolecular hydroamination reaction in good to excellent yields.

Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines

2017 ◽  
Vol 15 (21) ◽  
pp. 4686-4696 ◽  
Author(s):  
Sonu Kumar ◽  
Mohammad Mujahid ◽  
Akhilesh K. Verma
Keyword(s):  
Molecular Iodine ◽  
Reaction Conditions

A tandem approach for the synthesis of iodo benzo[a]phenazine derivatives using molecular iodine has been described under mild reaction conditions.

scholarly journals Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

2020 ◽  
Vol 16 ◽  
pp. 798-808
Author(s):  
Dong Cai ◽  
ZhiHua Zhang ◽  
Yufan Meng ◽  
KaiLi Zhu ◽  
LiYi Chen ◽  
...  
Keyword(s):  
Acetic Anhydride ◽  
Practical Method ◽  
Crystallographic Data ◽  
Glycyrrhetinic Acid ◽  
The Other ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Ester Derivative ◽  
Important Intermediate

In the present study, a practical method to prepare piperazinyl amides of 18β-glycyrrhetinic acid was developed. Two main procedures for the construction of important intermediate 8 are discussed. One procedure involves the amidation of 1-Boc-piperazine with 3-acetyl-18β-glycyrrhetinic acid, prepared by the reaction of 18β-glycyrrhetinic acid with acetic anhydride without any solvent at 130 °C. The other procedure to prepare compound 8 involves the amidation of 18β-glycyrrhetinic acid followed by the esterification with acetic anhydride. Finally, compound 8 underwent N-Boc deprotection to prepare product 4. To ascertain the scope of the reaction, another C-3 ester derivative 17 was tested under the optimized reaction conditions. Furthermore, the reasons for the appearance of byproducts were elucidated. Crystallographic data of a selected piperazinyl amide is reported.

scholarly journals Efficient synthesis of dihydropyrimidinones via a three-component Biginelli-type reaction of urea, alkylaldehyde and arylaldehyde

2013 ◽  
Vol 9 ◽  
pp. 2846-2851 ◽  
Author(s):  
Haijun Qu ◽  
Xuejian Li ◽  
Fan Mo ◽  
Xufeng Lin
Keyword(s):  
Molecular Iodine ◽  
Tandem Reaction ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Reaction Proceeds ◽  
Phosphoric Acids ◽  
Substituted Urea

A one-pot three-component synthesis of dihydropyrimidinones via a molecular iodine-catalyzed tandem reaction of simple readily available mono-substituted urea, alkylaldehyde, and arylaldehyde has been developed. The reaction proceeds with high chemo- and regioselectivity to give highly diverse dihydropyrimidinones in reasonable yields under mild reaction conditions. Moreover, the first catalytic enantioselective version of this reaction was also realized by using chiral spirocyclic SPINOL-phosphoric acids.

Molecular iodine as a mild catalyst for cross-coupling of alkenes and alcohols

2018 ◽  
Vol 90 (2) ◽  
pp. 377-386 ◽  
Author(s):  
Klara Čebular ◽  
Stojan Stavber
Keyword(s):  
Molecular Diversity ◽  
Bond Formation ◽  
Cross Coupling ◽  
Acid Catalyst ◽  
Molecular Iodine ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
Synthetic Procedure ◽  
Lewis Acid Catalyst ◽  
Solvent Free Reaction

Abstract C–C bond formation is one of the most fundamental approaches toward molecular diversity in organic synthesis. In pursuit of environmentally friendlier chemical approaches to organic chemistry, we present a new metal-free method for direct dehydrative cross-coupling of alcohols and alkenes using molecular iodine as a Lewis acid catalyst under solvent-free reaction conditions. The reaction is atom-economical, tolerant to air and allows simple synthetic procedure, furnishing Csp3–Csp2 coupling products with yields up to 97%. The method has proved efficient for coupling of secondary benzyl alcohols with phenyl-substituted alkenes.

Molecular iodine-catalysed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or sulfonamides

2009 ◽  
Vol 2009 (10) ◽  
pp. 638-641 ◽  
Author(s):  
Xufeng Lin ◽  
Jun Wang ◽  
Fangxi Xu ◽  
Yanguang Wang
Keyword(s):  
Reaction Time ◽  
Efficient Method ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Allylic Alcohols ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Metal Free ◽  
Amidation Reaction ◽  
Operational Simplicity

A highly efficient method for the C–N bond formation via 2 mol% of molecular iodine-catalysed amidation reaction of benzylic and allylic alcohols with carboxamides or sulfonamides in MeCN is described, giving the corresponding substituted amides and allylic amides in moderate to excellent yields. The significan features of the procedure include mild and metal-free reaction conditions, operational simplicity, inexpensive reagents, short reaction time, and good yields.

A Mild and Practical Method for Deprotection of Aryl Methyl/ Benzyl/Allyl Ethers with HPPh2 and tBuOK

2021 ◽  
Author(s):  
WenJing Pan ◽  
Chenchen Li ◽  
Haoyin Zhu ◽  
Fangfang Li ◽  
Tao Li ◽  
...  
Keyword(s):  
Practical Method ◽  
Reaction Conditions ◽  
Metal Free ◽  
Allyl Ethers ◽  
Aryl Ethers ◽  
Aryl Methyl ◽  
General Method

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2 and tBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good...

Molecular Iodine-Catalyzed Carbonyl-Olefin Metathesis

2018 ◽  
Author(s):  
Thanh Vinh Nguyen ◽  
Uyen P. N. Tran ◽  
Giulia Oss ◽  
Martin Breugst ◽  
Eric Detmar ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Olefin Metathesis ◽  
Functional Group ◽  
Molecular Iodine ◽  
Mechanistic Studies ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Elemental Iodine

The carbonyl-olefin metathesis reaction is a synthetically valuable transformation that could facilitate rapid functional group interconversion and construction of new organic structures. Herein we demonstrate that elemental iodine, a very simple and mild catalyst, can efficiently promote this chemical transformation under mild reaction conditions with excellent outcomes. Our mechanistic studies revealed intriguing aspects of iodine activation mode that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.

Catalyst-free Synthesis of Aminomethylphenol Derivatives in Cyclopentyl Methyl Ether via Petasis Borono-Mannich Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Jia-Qi Di ◽  
Hao-Jie Wang ◽  
Zhen-Shui Cui ◽  
Jin-Yong Hu ◽  
Zhan-Hui Zhang
Keyword(s):  
Secondary Amine ◽  
Methyl Ether ◽  
Mannich Reaction ◽  
Phenylboronic Acid ◽  
Functional Materials ◽  
Practical Method ◽  
Model Reaction ◽  
Arylboronic Acid ◽  
Reaction Conditions ◽  
Catalyst Free

Objective: Aminomethylphenol molecules have wider applications in pharmaceuticals, agrochemicals, plant protection and promising functional materials. The development of an efficient and practical method to prepare this class of compound is highly desirable from both environmental and economical points of views. Materials and Methods: In order to establish an effective synthetic method for preparing aminomethylphenol derivatives, the Petasis borono-Mannich reaction of salicylaldehyde, phenylboronic acid and 1,2,3,4-tetrahydroisoquinoline was selected as a model reaction. A variety of reaction conditions are investigated including solvent and temperature. The generality and limitation of the established method were also evaluated. Results and Discussion: It was found that model reaction can be carried out in cyclopentyl methyl ether at 80 oC under catalyst-free condition. This protocol with a broad substrate applicability, the reaction of various arylboronic acid, secondary amine and salicylaldehyde proceeded smoothly under optimal reaction conditions to afforded various aminomethylphenol derivatives in high yields. A practical, scalable, and high-yielding synthesis of aminomethylphenol derivatives was successfully accomplished. Conclusion: A catalyst-free practical method for the synthesis of minomethylphenol derivatives based on Petasis borono– Mannich (PBM) reaction of various arylboronic acid, secondary amine and salicylaldehyde in cyclopentyl methyl ether has been developed. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use cyclopentyl methyl ether as the reaction medium, clean reaction profiles, easy operation, and high to excellent yield.

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