Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex

2019 ◽  
Vol 17 (37) ◽  
pp. 8522-8526 ◽  
Author(s):  
Toshitaka Okamura ◽  
Shogo Fujiki ◽  
Yoshiharu Iwabuchi ◽  
Naoki Kanoh
Keyword(s):  
Aromatic Molecules ◽  
Nicholas Reaction ◽  
Stable Reagent ◽  
Dicobalt Hexacarbonyl

A benchtop-stable reagent for the catalytic Nicholas reaction with aromatic molecules was developed.

Efficient Synthesis of O-tert-Propargylic Oximes via Nicholas Reaction

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3461-3465
Author(s):  
Itaru Nakamura ◽  
Keigo Shiga ◽  
Mao Suzuki ◽  
Masahiro Terada
Keyword(s):  
Ammonium Nitrate ◽  
Efficient Synthesis ◽  
Propargylic Alcohols ◽  
Cyclic Nitrones ◽  
Acidic Catalysts ◽  
Nicholas Reaction ◽  
High Yields ◽  
Dicobalt Hexacarbonyl ◽  
Cerium Iv Ammonium Nitrate

A synthetic protocol to access O-tert-propargylic oximes derived from tertiary propargylic alcohols was established via Nicholas reaction. Thus, BF3·OEt2-mediated reaction between the dicobalt hexacarbonyl complex of tert-propargylic alcohols and p-nitrobenzaldoxime followed by decomplexation with cerium(IV) ammonium nitrate afforded the corresponding O-tert-propargylic oximes in good to high yields. The obtained O-tert-propargylic oximes were effectively converted into heterocycles, such as four-membered cyclic nitrones, oxazepines, and isoxazolines, by using π-Lewis acidic catalysts.

scholarly journals Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

2020 ◽  
Vol 16 ◽  
pp. 1-8 ◽  
Author(s):  
Renata Kaczmarek ◽  
Dariusz Korczyński ◽  
James R Green ◽  
Roman Dembinski
Keyword(s):  
Bond Formation ◽  
Side Chain ◽  
Nicholas Reaction ◽  
Propargyl Ether ◽  
Dicobalt Hexacarbonyl

Dicobalt hexacarbonyl nucleoside complexes of propargyl ether or esters of 5-substituted uridines react with diverse C-nucleophiles. Synthetic outcomes confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series.

scholarly journals Nicholas Reactions of Alkynyl- and Alkenyltrifluoroborates

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2923-2927 ◽  
Author(s):  
Brent Onge ◽  
James Green
Keyword(s):  
Lewis Acid ◽  
Nicholas Reaction ◽  
Dicobalt Hexacarbonyl

The Lewis acid mediated Nicholas reaction of potassium alkynyltrifluoroborates and propargyl acetate-hexacarbonyldicobalt complexes affords 1,4-diyne dicobalt hexacarbonyl complexes in good yields. The analogous Nicholas reactions of potassium alkenyltrifluoro­borates give 1,3-enyne dicobalt hexacarbonyl complexes in most cases, although the initial site of reaction can vary. Potassium vinyltrifluoroborate itself affords alkynylcyclopropane complexes.

Triphenylmethyldifluoramine: A Stable Reagent for the Synthesis of gem-Bis(difluoramines)

2002 ◽  
Author(s):  
G. K. Prakash ◽  
Markus Etzkorn ◽  
George A. Olah ◽  
Karl O. Christe ◽  
Stefan Schneider
Keyword(s):  
Stable Reagent
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