scholarly journals Nickel-Catalyzed Multicomponent Coupling of Butadiene, Aldehydes, Alkynes and Schwartz Reagent to Form 1,4-Dienes

2021 ◽  
pp. 1939
Author(s):  
Yu-Qing Li ◽  
Shi-Liang Shi
Keyword(s):  
Schwartz Reagent ◽  
Multicomponent Coupling

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

scholarly journals PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

2011 ◽  
Vol 7 ◽  
pp. 1334-1341 ◽  
Author(s):  
Sanny Verma ◽  
Suman L Jain ◽  
Bir Sain
Keyword(s):  
Coupling Reaction ◽  
Recyclable Catalyst ◽  
Efficient Synthesis ◽  
Molecular Bromine ◽  
Keto Ester ◽  
One Step ◽  
High Yields ◽  
Multicomponent Coupling ◽  
Three Component Coupling

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.

scholarly journals Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

2015 ◽  
Vol 6 (11) ◽  
pp. 6086-6090 ◽  
Author(s):  
Matthew A. Horwitz ◽  
Naoya Tanaka ◽  
Takuya Yokosaka ◽  
Daisuke Uraguchi ◽  
Jeffrey S. Johnson ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Multicomponent Coupling Reactions ◽  
Multicomponent Coupling

A reductive coupling of two different carbonyls via a polar two-electron reaction mechanism was developed and the stereochemical outcome of this multicomponent process is precisely controlled by a chiral triaminoiminophosphorane.

ChemInform Abstract: Regio- and Stereoselective Multicomponent Coupling Reaction of Alkynes and Dimethylzinc Involving Allylnickelacycles.

ChemInform ◽  
2012 ◽  
Vol 43 (47) ◽  
pp. no-no
Author(s):  
Takamichi Mori ◽  
Toshiyuki Nakamura ◽  
Gen Onodera ◽  
Masanari Kimura
Keyword(s):  
Coupling Reaction ◽  
Multicomponent Coupling

ChemInform Abstract: A Multicomponent Coupling Reaction Induced by Insertion of Arynes into the C=O Bond of Formamide.

ChemInform ◽  
2011 ◽  
Vol 42 (48) ◽  
pp. no-no
Author(s):  
Eito Yoshioka ◽  
Shigeru Kohtani ◽  
Hideto Miyabe
Keyword(s):  
Coupling Reaction ◽  
Multicomponent Coupling

C–N Ring Construction: The Waser Synthesis of Jerantinine E

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Ni Catalyst ◽  
University Of Alberta ◽  
Princeton University ◽  
In Situ Preparation ◽  
National University ◽  
The University ◽  
École Polytechnique ◽  
Pais Vasco ◽  
Multicomponent Coupling

James A. Bull of Imperial College London prepared (J. Org. Chem. 2013, 78, 6632) the aziridine 2 with high diastereocontrol by adding the anion of diiodomethane to the imine 1. Karl Anker Jørgensen of Aarhus University observed (Chem. Commun. 2013, 49, 6382) high ee in the distal aziridination of 3 to give 4. Benito Alcaide of the Universidad Complutense de Madrid and Pedro Almendros of ICOQ- CSIC Madrid reduced (Adv. Synth. Catal. 2013, 355, 2089) the β-lactam 5 to the azetidine 6. Hiroaki Sasai of Osaka University added (Org. Lett. 2013, 15, 4142) the allenoate 8 to the imine 7, delivering the azetidine 9 in high ee. Tamio Hayashi of Kyoto University, the National University of Singapore, and A*STAR devised (J. Am. Chem. Soc. 2013, 135, 10990) a Pd catalyst for the enanti­oselective addition of the areneboronic acid 11 to the pyrroline 10 to give 12. Ryan A. Brawn of Pfizer (Org. Lett. 2013, 15, 3424) reported related results. Nicolai Cramer of the Ecole Polytechnique Fédérale de Lausanne developed (J. Am. Chem. Soc. 2013, 135, 11772) a Ni catalyst for the cyclization of the formamide 13 to the lactam 14. Andrew D. Smith of the University of St. Andrews used (Org. Lett. 2013, 15, 3472) an organocatalyst to cyclize 15 to 16. Jose L. Vicario of the Universidad del Pais Vasco effected (Synthesis 2013, 45, 2669) the multicomponent coupling of 17, 18, and 19, mediated by an organocatalyst, to construct 20 in high ee. André Beauchemin of the University of Ottawa explored (J. Org. Chem. 2013, 78, 12735) the thermal cyclization of ω-alkenyl hydroxyl amines such as 21. Abigail G. Doyle of Princeton University developed (Angew. Chem. Int. Ed. 2013, 52, 9153) a Ni catalyst for the enantioselective addition of aryl zinc bromides such as 24 to the pro­chiral 23, to give 25 in high ee. Dennis G. Hall of the University of Alberta developed (Angew. Chem. Int. Ed. 2013, 52, 8069) an in situ preparation of the allyl boronate 26 in high ee. Addition to the aldehyde 27 proceeded with high diasteroselectivity.

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