Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3446-3451
Author(s):  
Songlin Zhang ◽  
Dengbing Xie ◽  
Yiqiong Wang ◽  
Bo Yang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
Carbon Double Bond ◽  
Allyl Halides ◽  
First Time

The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1437-1441
Author(s):  
Xu yan Cao ◽  
Fei Huang ◽  
Songlin Zhang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Mild Conditions ◽  
Allyl Halides ◽  
Barbier Reaction

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

Palladium-promoted sulfur atom migration on carboranes: facile B(4)−S bond formation from mononuclear Pd-B(4) complexes

2018 ◽  
Vol 90 (4) ◽  
pp. 607-616
Author(s):  
Yin-Ping Wang ◽  
Yue-Jian Lin ◽  
Guo-Xin Jin
Keyword(s):  
Sulfur Atom ◽  
Bond Formation ◽  
Reaction Process ◽  
One Pot ◽  
Leaving Group ◽  
Atom Migration ◽  
First Time

AbstractFor the first time, carborane complexes containing a B(4)–S bond were obtained directly by heating mononuclear Pd-B(4)-bound carborane complexes. A possible mechanism involved in sulfur atom migration is presented in which the leaving group, pyridine, benzyl isocyanide or PPh3, is demonstrated to be the trigger of the reaction process. In this work, efficient routes are developed through one-pot reactions to prepare B(4)-S carborane derivatives.

Sequential Michael addition/retro-Claisen condensation of aromatic β-diketones with α,β-unsaturated esters: an approach to obtain 1,5-ketoesters

2016 ◽  
Vol 14 (8) ◽  
pp. 2390-2394 ◽  
Author(s):  
Gui-Xin Cai ◽  
Jing Wen ◽  
Ting-Ting Lai ◽  
Dan Xie ◽  
Cheng-He Zhou
Keyword(s):  
Michael Addition ◽  
Bond Formation ◽  
One Pot ◽  
Claisen Condensation ◽  
Unsaturated Esters ◽  
Mild Conditions

A K2CO3-catalyzed one-pot protocol involving sequential C–C bond formation and cleavage of aromatic β-diketones with α,β-unsaturated esters is developed to obtain 1,5-ketoesters, proceeding smoothly under mild conditions in up to 98% isolated yield.

One pot oxidative N–S bond formation to access 2-sulfenylimine chromenes

2016 ◽  
Vol 14 (2) ◽  
pp. 582-589 ◽  
Author(s):  
Ashok Kale ◽  
Madhu Chennapuram ◽  
Chiranjeevi Bingi ◽  
Jagadeesh Babu Nanubolu ◽  
Krishnaiah Atmakur
Keyword(s):  
Bond Formation ◽  
Reaction Conditions ◽  
One Pot ◽  
Simple Reaction ◽  
Catalyst Free

Synthesis of 2-sulfenylimine chromene compounds is accomplished in a one-pot, catalyst-free, five-component reaction in toluene. When aniline was employed as nucleophile formation of hexahydrobenzofuran-2-N-phenyl carboxamide was observed. Excellent yields, simple reaction conditions high compatibility are the advantages of this protocol.

Catalytic CSe Bond Formation under Very Mild Conditions for the Two-Step, One-Pot Synthesis of Aryl Selenoacetates

2012 ◽  
Vol 354 (14-15) ◽  
pp. 2653-2658 ◽  
Author(s):  
Konstantin Grenader ◽  
Björn Schüpbach ◽  
Annabell Peters ◽  
Oliver Kümmel ◽  
Oliver Halter ◽  
...  
Keyword(s):  
Bond Formation ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis
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