scholarly journals C2-Alkylation of N-pyrimidylindole with vinylsilane via cobalt-catalyzed C–H bond activation

2012 ◽  
Vol 8 ◽  
pp. 1536-1542 ◽  
Author(s):  
Zhenhua Ding ◽  
Naohiko Yoshikai

Direct C2-alkylation of an indole bearing a readily removable N-pyrimidyl group with a vinylsilane was achieved by using a cobalt catalyst generated in situ from CoBr2, bathocuproine, and cyclohexylmagnesium bromide. The reaction allows coupling between a series of N-pyrimidylindoles and vinylsilanes at a mild reaction temperature of 60 °C, affording the corresponding alkylated indoles in moderate to good yields.

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Chia-Yu Huang ◽  
Jianbin Li ◽  
Chao-Jun Li

AbstractHydrogen atom abstraction (HAT) from C(sp3)–H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs since involving stoichiometric oxidants, excessive alkane loading, and limited scope are common drawbacks. Here we report a photo-induced and chemical oxidant-free cross-dehydrogenative coupling (CDC) between alkanes and heteroarenes using catalytic chloride and cobalt catalyst. Couplings of strong C(sp3)–H bond-containing substrates and complex heteroarenes, have been achieved with satisfactory yields. This dual catalytic platform features the in situ engendered chlorine radical for alkyl radical generation and exploits the cobaloxime catalyst to enable the hydrogen evolution for catalytic turnover. The practical value of this protocol was demonstrated by the gram-scale synthesis of alkylated heteroarene with merely 3 equiv. alkane loading.


ChemInform ◽  
2009 ◽  
Vol 40 (44) ◽  
Author(s):  
Remi Martinez ◽  
Marc-Olivier Simon ◽  
Reynald Chevalier ◽  
Cyrielle Pautigny ◽  
Jean-Pierre Genet ◽  
...  

2011 ◽  
Vol 171 (1) ◽  
pp. 186-191 ◽  
Author(s):  
Amélie Rochet ◽  
Virginie Moizan ◽  
Christophe Pichon ◽  
Fabrice Diehl ◽  
Adrien Berliet ◽  
...  

2002 ◽  
Vol 730 ◽  
Author(s):  
J.Z. Luo ◽  
P. Chen ◽  
Z.T. Xiong ◽  
K.L. Tan ◽  
J.Y. Lin

AbstractA remarkable reduction in reaction temperature was found for the hydrogenation of Li metal in Li-C mixture. H2 uptake started at 50°C, became vigorous at 150°C and slowed down at temperatures above 200°C. In-situ XRD characterizations revealed that Li-C intercalation compounds such as LiC6 and LiC12 existed in the Li-C samples, and LiH formed after the hydrogenation taking place. Increasing the carbon content in the Li-C mixture, from Li/C = 10:1 to 5:1 and then to 2:1, would enhance the reactivity of hydrogenation accordingly. Carbon nanotubes, with smaller size and larger specific area, showed even greater enhancement of the hydrogenation of lithium metal than graphite. The mechanism for the low temperature hydrogenation of Li-C samples was studied and discussed.


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