Total Synthesis of Hibispeptin A via Pd-Catalyzed C(sp3)–H Arylation with Sterically Hindered Aryl Iodides

2014 ◽  
Vol 16 (24) ◽  
pp. 6488-6491 ◽  
Author(s):  
Gang He ◽  
Shu-Yu Zhang ◽  
William A. Nack ◽  
Ryan Pearson ◽  
Javon Rabb-Lynch ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aryl Iodides ◽  
Sterically Hindered

scholarly journals Cu(I)- and Pd(0)-Catalyzed Arylation of Oxadiamines with Fluorinated Halogenobenzenes: Comparison of Efficiency

Molecules ◽  
2020 ◽  
Vol 25 (5) ◽  
pp. 1084 ◽  
Author(s):  
Maria S. Lyakhovich ◽  
Alexei D. Averin ◽  
Olga K. Grigorova ◽  
Vitaly A. Roznyatovsky ◽  
Olga A. Maloshitskaya ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Halogen Atoms ◽  
Aryl Iodides ◽  
Aryl Bromides ◽  
Sterically Hindered ◽  
Catalyzed Reactions

The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their N,N′-diaryl derivatives was carried out. The dependence of the reactivity of the aryl halides on the nature of the substituents and halogen atoms as well as on the structure of oxadiamines was investigated. It was found that the copper-catalyzed reactions were somewhat comparable with the palladium-mediated processes in the majority of cases, especially in the reactions with para-fluorine- and para-(trifluoromethyl)-substituted aryl halides, although the necessity to use aryl iodides in the Cu(I)-catalyzed amination was obvious. Pd catalysis was found inevitable for the successful amination of more sterically hindered ortho-(trifluoromethyl)aryl bromides.

scholarly journals Carbonylative Cross-Coupling ofortho-Disubstituted Aryl Iodides. Convenient Synthesis of Sterically Hindered Aryl Ketones

2008 ◽  
Vol 10 (22) ◽  
pp. 5301-5304 ◽  
Author(s):  
B. Michael O’Keefe ◽  
Nicholas Simmons ◽  
Stephen F. Martin
Keyword(s):  
Cross Coupling ◽  
Aryl Iodides ◽  
Convenient Synthesis ◽  
Aryl Ketones ◽  
Sterically Hindered

Total synthesis of zincophorin methyl ester. Stereocontrol of 1,2-induction using sterically hindered enoxysilanes

Tetrahedron ◽  
2015 ◽  
Vol 71 (4) ◽  
pp. 709-726 ◽  
Author(s):  
François Godin ◽  
Philippe Mochirian ◽  
Gabrielle St-Pierre ◽  
Yvan Guindon
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Sterically Hindered

scholarly journals Thiourea-catalyzed Diels–Alder reaction of a naphthoquinone monoketal dienophile

2013 ◽  
Vol 9 ◽  
pp. 1414-1418 ◽  
Author(s):  
Carsten S Kramer ◽  
Stefan Bräse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Selective Synthesis ◽  
Quaternary Center ◽  
Diels Alder Reaction ◽  
Cycloaddition Product ◽  
Sterically Hindered ◽  
First Time

A variety of organocatalysts were screened for the catalysis of the naphthoquinone monoketal Diels–Alder reaction. In this study we found that Schreiner's thiourea catalyst 10 and Jacobson's thiourea catalyst 12 facilitate the cycloaddition of the sterically hindered naphthoquinone monoketal dienophile 3 with diene 4. The use of thiourea catalysis allowed for the first time the highly selective synthesis of the exo-product 2a in up to 63% yield. In this reaction a new quaternary center was built. The so formed cycloaddition product 2a represents the ABC tricycle of beticolin 0 (1) and is also a valuable model substrate for the total synthesis of related natural products.

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