Gold-Catalyzed Sigmatropic Rearrangement Reactions via Carbene Transfer Reactions

2020 ◽  
Vol 85 (18) ◽  
pp. 11882-11891 ◽  
Author(s):  
Feifei He ◽  
Sripati Jana ◽  
Rene M. Koenigs
Keyword(s):  
Sigmatropic Rearrangement ◽  
Transfer Reactions ◽  
Carbene Transfer ◽  
Rearrangement Reactions

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4348-4358 ◽  
Author(s):  
Fang Li ◽  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Sigmatropic Rearrangement ◽  
Tertiary Amines ◽  
Amino Esters ◽  
Catalyst Free ◽  
Rearrangement Reaction ◽  
Rearrangement Reactions ◽  
Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

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

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>

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

scholarly journals Gold Complexes with ADAP Ligands: Effect of Bulkiness in Catalytic Carbene Transfer Reactions (ADAP = Alkoxydiaminophosphine)

2020 ◽  
Vol 39 (13) ◽  
pp. 2553-2559
Author(s):  
Juan Diego Pizarro ◽  
Francisco Molina ◽  
Manuel R. Fructos ◽  
Pedro J. Pérez
Keyword(s):  
Transfer Reactions ◽  
Gold Complexes ◽  
Carbene Transfer
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