Metal-free iodine-promoted direct synthesis of unsymmetrical triarylmethanes

2020 ◽  
Vol 44 (14) ◽  
pp. 5519-5525
Author(s):  
Ying-Chun Gu ◽  
Jie Huang ◽  
Run-Shi Wu ◽  
Qi Yang ◽  
Ya-Qin Yu ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
One Pot ◽  
Metal Free ◽  
Free Iodine

Completely unsymmetrical triarylmethanes were prepared in a one-pot reaction via o-QM intermediates generated in situ.

Molybdenum-Mediated One-Pot Synthesis of Pyrazoles from Isoxazoles

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3796-3804 ◽  
Author(s):  
Marine Rey ◽  
Stéphane Beaumont
Keyword(s):  
Bond Cleavage ◽  
Direct Synthesis ◽  
Molybdenum Complex ◽  
One Pot ◽  
One Pot Synthesis ◽  
Wide Range ◽  
Hydrolysis Of ◽  
Substituted Pyrazoles

A one-pot approach for the direct synthesis of substituted pyrazoles from isoxazoles is reported. The process involves isoxazole N–O bond cleavage mediated by a molybdenum complex, in situ hydrolysis of the resulting β-amino enone to the corresponding 1,3-diketone, followed by pyrazole formation in the presence of hydrazine or substituted hydrazine. Good to excellent yields and regioselectivities are obtained with nonsymmetric isoxazoles. By using readily available starting materials, a wide range of substituted pyrazoles may be synthesized by this method.

scholarly journals Straightforward Strategies for the Preparation of NH-Sulfox­imines: A Serendipitous Story

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2525-2538 ◽  
Author(s):  
James Bull ◽  
Renzo Luisi ◽  
Leonardo Degennaro
Keyword(s):  
Transition Metal ◽  
Physicochemical Properties ◽  
Direct Synthesis ◽  
Transition Metal Catalysts ◽  
Hypervalent Iodine ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
New Procedures

Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.1 Introduction2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts3 Metal-Free Strategies to Prepare NH-Sulfoximines4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides5 Further Applications6 Conclusion

scholarly journals One-Pot NBS-Promoted Synthesis of Imidazoles and Thiazoles from Ethylarenes in Water

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 893 ◽  
Author(s):  
Liang Chen ◽  
Huajian Zhu ◽  
Jiang Wang ◽  
Hong Liu
Keyword(s):  
One Pot ◽  
Metal Free ◽  
Reaction Proceeds ◽  
In Situ Formation

A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.

Aryne insertion into the PO bond: one-pot synthesis of quaternary phosphonium triflates

2019 ◽  
Vol 17 (26) ◽  
pp. 6450-6460 ◽  
Author(s):  
Kashmiri Neog ◽  
Dhiraj Dutta ◽  
Babulal Das ◽  
Pranjal Gogoi
Keyword(s):  
Transition Metal ◽  
Phosphine Oxide ◽  
Direct Synthesis ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Synthetic Strategy

A novel transition-metal free synthetic strategy for the direct synthesis of quaternary phosphonium triflates via insertion of aryne into phosphine oxide.

scholarly journals Direct synthesis of the Janus-head ligand (MePy)3Sn–Sn(MePy)3using an unusual pyridyl-transfer reaction (MePy = 6-methyl-2-pyridyl)

2014 ◽  
Vol 43 (39) ◽  
pp. 14529-14532 ◽  
Author(s):  
Raúl García-Rodríguez ◽  
Dominic S. Wright
Keyword(s):  
Transfer Reaction ◽  
Direct Synthesis ◽  
Metal Oxidation ◽  
One Pot

Thein situreaction of the tripodal anion [EtAl(MePy)3]−(MePy = 6-Me-2-py) with SnCl2gives the Janus-head ligand (MePy)3Sn–Sn(MePy)3, containing a Sn–Sn bond, through a novel, one-pot reaction involving a combination of pyridyl transfer and metal-oxidation.

An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1071-1075 ◽  
Author(s):  
Vit Lellek ◽  
Cheng-yi Chen ◽  
Wanggui Yang ◽  
Jie Liu ◽  
Xuebao Ji ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions ◽  
Free Process ◽  
One Pot Condensation ◽  
Substituted Pyrazoles

An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles by simply heating pyrazolines in DMSO under oxygen.

scholarly journals Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

2017 ◽  
Vol 13 ◽  
pp. 910-918 ◽  
Author(s):  
Adrián A Heredia ◽  
Alicia B Peñéñory
Keyword(s):  
Substitution Reaction ◽  
Alkyl Halides ◽  
Indole Derivatives ◽  
Terminal Alkynes ◽  
Successive Reaction ◽  
One Pot ◽  
Metal Free ◽  
Substituted Acetylenes ◽  
In Situ Generation

Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides as starting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation of dialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction between KSeCN and alkyl halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted acetylenes.

Iodine-promoted one pot reaction of pyridin-2-amine with arylmethyl ketone and selenosulfonate: synthesis of 3-(alkylselanyl)-2-arylimidazo[1,2-a]pyridine under transition-metal free conditions

2019 ◽  
Vol 6 (5) ◽  
pp. 654-659 ◽  
Author(s):  
Nan Jiang ◽  
Yi Fang ◽  
Yue Fang ◽  
Shun-Yi Wang ◽  
Shun-Jun Ji
Keyword(s):  
Transition Metal ◽  
One Pot ◽  
Metal Free ◽  
Efficient Approach

A new efficient approach for the I2 promoted selenium functionalization of in situ generated imidazoheterocycles utilizing aliphatic selenosulfonate as the selenium source under transition metal-free conditions is developed.

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