A Gold Catalyst for Carbene-Transfer Reactions from Ethyl Diazoacetate

2005 ◽  
Vol 117 (33) ◽  
pp. 5418-5422 ◽  
Author(s):  
Manuel R. Fructos ◽  
Tomás R. Belderrain ◽  
Pierre de Frémont ◽  
Natalie M. Scott ◽  
Steven P. Nolan ◽  
...  
Keyword(s):  
Gold Catalyst ◽  
Transfer Reactions ◽  
Ethyl Diazoacetate ◽  
Carbene Transfer

A Gold Catalyst for Carbene-Transfer Reactions from Ethyl Diazoacetate

2005 ◽  
Vol 44 (33) ◽  
pp. 5284-5288 ◽  
Author(s):  
Manuel R. Fructos ◽  
Tomás R. Belderrain ◽  
Pierre de Frémont ◽  
Natalie M. Scott ◽  
Steven P. Nolan ◽  
...  
Keyword(s):  
Gold Catalyst ◽  
Transfer Reactions ◽  
Ethyl Diazoacetate ◽  
Carbene Transfer

scholarly journals C-H Functionalization Reactions of Unprotected N-Heterocycles by Gold Catalyzed Carbene Transfer

2020 ◽  
Author(s):  
Sripati Jana ◽  
Claire Empel ◽  
Chao Pei ◽  
Polina Aseeva ◽  
Thanh Vinh Nguyen ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Functional Groups ◽  
Gold Catalyst ◽  
Protecting Groups ◽  
Transfer Reactions ◽  
Mechanistic Studies ◽  
Economic Strategies ◽  
Carbene Transfer ◽  
Functionalization Reaction

<p>The C-H functionalization reaction of N-heterocycles with unprotected N-H group is one of the most step-economic strategies to introduce functional groups without the need of installation and removal of protecting groups. Despite recent significant advances in C-H functionalization chemistry, this strategy remains unsatisfactorily developed. In this report, we disclose a simple and straightforward protocol to allow for the selective C-H functionalization of unprotected double benzannellated N-heterocycles via gold catalyzed carbene transfer reactions (29 examples, up to 86% yield). The scope of the reaction can also be expanded to the corresponding protected heterocycles (37 examples, up to 98% yield), further demonstrating the generality of this method. Mechanistic studies by DFT calculations underpin the importance of the gold catalyst and reveal that the selectivity of this reaction is driven by trace amounts of water present in the reaction mixture.</p>

Complete Control of the Chemoselectivity in Catalytic Carbene Transfer Reactions from Ethyl Diazoacetate:  AnN-Heterocyclic Carbene−Cu System That Suppresses Diazo Coupling

2004 ◽  
Vol 126 (35) ◽  
pp. 10846-10847 ◽  
Author(s):  
Manuel R. Fructos ◽  
Tomás R. Belderrain ◽  
M. Carmen Nicasio ◽  
Steven P. Nolan ◽  
Harneet Kaur ◽  
...  
Keyword(s):  
Transfer Reactions ◽  
Complete Control ◽  
Ethyl Diazoacetate ◽  
Diazo Coupling ◽  
Carbene Transfer

scholarly journals Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents

2021 ◽  
Author(s):  
Lucie Cailler ◽  
Andrey P. Kroitor ◽  
Alexander G. Martynov ◽  
Yulia G. Gorbunova ◽  
Alexander B. Sorokin
Keyword(s):  
Transfer Reactions ◽  
Ethyl Diazoacetate ◽  
Wide Range ◽  
Carbene Transfer ◽  
Aromatic Heterocyclic

Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and...

scholarly journals Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate

2015 ◽  
Vol 11 ◽  
pp. 2254-2260 ◽  
Author(s):  
Manuel R Fructos ◽  
Juan Urbano ◽  
M Mar Díaz-Requejo ◽  
Pedro J Pérez
Keyword(s):  
Coordination Sphere ◽  
Outer Sphere ◽  
Transfer Reactions ◽  
Ethyl Diazoacetate ◽  
Inner Sphere ◽  
Carbene Transfer ◽  
Catalyzed Reactions ◽  
Sphere Mechanism ◽  
Nitrogen Evolution

Kinetic experiments based on the measurement of nitrogen evolution in the reaction of ethyl diazoacetate (N2CHCO2Et, EDA) and styrene or methanol catalyzed by the [IPrAu]+ core (IPr = 1,3-bis(diisopropylphenyl)imidazole-2-ylidene) have provided evidence that the transfer of the carbene group CHCO2Et to the substrate (styrene or methanol) takes place in the coordination sphere of Au(I) by means of an inner-sphere mechanism, in contrast to the generally accepted proposal of outer-sphere mechanisms for Au(I)-catalyzed reactions.

scholarly journals C-H Functionalization Reactions of Unprotected N-Heterocycles by Gold Catalyzed Carbene Transfer

2020 ◽  
Author(s):  
Sripati Jana ◽  
Claire Empel ◽  
Chao Pei ◽  
Polina Aseeva ◽  
Thanh Vinh Nguyen ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Functional Groups ◽  
Gold Catalyst ◽  
Protecting Groups ◽  
Transfer Reactions ◽  
Mechanistic Studies ◽  
Economic Strategies ◽  
Carbene Transfer ◽  
Functionalization Reaction

<p>The C-H functionalization reaction of N-heterocycles with unprotected N-H group is one of the most step-economic strategies to introduce functional groups without the need of installation and removal of protecting groups. Despite recent significant advances in C-H functionalization chemistry, this strategy remains unsatisfactorily developed. In this report, we disclose a simple and straightforward protocol to allow for the selective C-H functionalization of unprotected double benzannellated N-heterocycles via gold catalyzed carbene transfer reactions (29 examples, up to 86% yield). The scope of the reaction can also be expanded to the corresponding protected heterocycles (37 examples, up to 98% yield), further demonstrating the generality of this method. Mechanistic studies by DFT calculations underpin the importance of the gold catalyst and reveal that the selectivity of this reaction is driven by trace amounts of water present in the reaction mixture.</p>

Site-Directed Anchoring of an N-Heterocyclic Carbene on a Dimetal Platform: Evaluation of a Pair of Diruthenium(I) Catalysts for Carbene-Transfer Reactions from Ethyl Diazoacetate

2011 ◽  
Vol 30 (7) ◽  
pp. 2051-2058 ◽  
Author(s):  
Biswajit Saha ◽  
Tapas Ghatak ◽  
Arup Sinha ◽  
S. M. Wahidur Rahaman ◽  
Jitendra K. Bera
Keyword(s):  
Transfer Reactions ◽  
Ethyl Diazoacetate ◽  
Carbene Transfer

Catalyst-Controlled Site-Selective N-H and C3-Arylation of Carba-zole via Carbene Transfer Reactions

2021 ◽  
Author(s):  
Sourav Sekhar Bera ◽  
Srishti Ballabh Bahukhandi ◽  
Claire Empel ◽  
Rene M Koenigs
Keyword(s):  
Transfer Reactions ◽  
Palladium Acetate ◽  
Direct Arylation ◽  
Carbene Transfer ◽  
A Site ◽  
Site Selective

A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed. While Au(I)-NHC catalysts lead to selective C3-arylation, palladium acetate allows for selective N-H arylation, displaying...

Carbene transfer reactions between transition-metal ions

1999 ◽  
Vol 28 (5) ◽  
pp. 315-322 ◽  
Author(s):  
Shiuh-Tzung Liu ◽  
K. Rajender Reddy
Keyword(s):  
Transition Metal ◽  
Metal Ions ◽  
Transition Metal Ions ◽  
Transfer Reactions ◽  
Carbene Transfer

Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors

ACS Catalysis ◽  
2021 ◽  
pp. 442-452
Author(s):  
Ayan Dasgupta ◽  
Emma Richards ◽  
Rebecca L. Melen
Keyword(s):  
Transfer Reactions ◽  
Carbene Transfer
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