NHC-Iridium-Catalyzed Deoxygenative Coupling of Primary Alcohols Producing Alkanes Directly: Synergistic Hydrogenation with Sodium Formate Generated in Situ

ACS Catalysis ◽  
2021 ◽  
pp. 10796-10801
Author(s):  
Zeye Lu ◽  
Qingshu Zheng ◽  
Siqi Yang ◽  
Chun Qian ◽  
Yajing Shen ◽  
...  
2019 ◽  
Vol 216 ◽  
pp. 373-381 ◽  
Author(s):  
Xianpu Zhu ◽  
Qin Cao ◽  
Yichao Chen ◽  
Xiaoying Sun ◽  
Xiaofeng Liu ◽  
...  

1993 ◽  
Vol 353 (1-2) ◽  
pp. 81-100 ◽  
Author(s):  
E. Pastor ◽  
S. Wasmus ◽  
T. Iwasita ◽  
M.C. Arévalo ◽  
S. González ◽  
...  

2014 ◽  
Vol 43 (46) ◽  
pp. 17248-17254 ◽  
Author(s):  
Jong-Hoo Choi ◽  
Leo E. Heim ◽  
Mike Ahrens ◽  
Martin H. G. Prechtl

In this work, we present a mild method for direct conversion of primary alcohols into carboxylic acids with the use of water as an oxygen source.


Synlett ◽  
2007 ◽  
Vol 2007 (10) ◽  
pp. 1565-1568 ◽  
Author(s):  
Philip Page ◽  
Louise Appleby ◽  
Benjamin Buckley ◽  
Steven Allin ◽  
Michael McKenzie

2021 ◽  
Author(s):  
Alyah Chmiel ◽  
Oliver P. Williams ◽  
Colleen Chernowsky ◽  
Charles Yeung ◽  
Zachary Wickens

We describe a photocatalytic system that elicits potent photoreductant activity from conventional photocatalysts by leveraging radical anion intermediates generated <i>in situ</i>. The combination of isophthalonitrile and sodium formate promotes diverse aryl radical coupling reactions from abundant but difficult to reduce aryl chloride substrates. Mechanistic studies reveal two parallel pathways for substrate reduction both enabled by a key terminal reductant byproduct, carbon dioxide radical anion.


2020 ◽  
Author(s):  
Xiao-Bing Lan ◽  
Zongren Ye ◽  
Weikang Li ◽  
Jiahao Liu ◽  
Ming Huang ◽  
...  

The implementation of earth-abundant metals mediated chemistry is a major goal in homogeneous catalysis. Borrowing hydrogen/hydrogen autotransfer (BH/HA) reaction, as a straightforward and sustainable synthetic method, has attracted considerable attention in the development of earth-abuandant metal catalysts. Herein, we report a tungsten-catalyzed <i>N</i>-alkylation reaction of amines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)<sub>4</sub> (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible <i>in-situ</i> catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups, especially the challenging substrates with sterically hindered substituents, or heteroatoms. Mechanistic insights based on experimental and computational studies are also provided.


2020 ◽  
Author(s):  
Xiao-Bing Lan ◽  
Zongren Ye ◽  
Weikang Li ◽  
Jiahao Liu ◽  
Ming Huang ◽  
...  

The implementation of earth-abundant metals mediated chemistry is a major goal in homogeneous catalysis. Borrowing hydrogen/hydrogen autotransfer (BH/HA) reaction, as a straightforward and sustainable synthetic method, has attracted considerable attention in the development of earth-abuandant metal catalysts. Herein, we report a tungsten-catalyzed <i>N</i>-alkylation reaction of amines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)<sub>4</sub> (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible <i>in-situ</i> catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups, especially the challenging substrates with sterically hindered substituents, or heteroatoms. Mechanistic insights based on experimental and computational studies are also provided.


2013 ◽  
Vol 165 ◽  
pp. 63-69 ◽  
Author(s):  
Miral Shah ◽  
Hyuk Taek Kwon ◽  
Vu Tran ◽  
Sonny Sachdeva ◽  
Hae-Kwon Jeong

Catalysts ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1317
Author(s):  
Alena Krupková ◽  
Klára Kubátová ◽  
Lucie Červenková Šťastná ◽  
Petra Cuřínová ◽  
Monika Müllerová ◽  
...  

Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbene (NHC) precursors. Catalytic activity of model and dendritic NHCs generated in situ by deprotonation with DBU was tested in redox esterification of α,β-unsaturated aldehydes and the influence of substitution, dendrimer generation, temperature and substrate structure on the reaction outcome was evaluated. Dipp substituted NHCs showed high activity and selectivity in the reaction with primary alcohols. Effectiveness of organic solvent nanofiltration for the recycling of dendritic NHCs was demonstrated on the 1st generation Dipp substituted catalyst in model redox esterification of cinnamaldehyde with benzyl alcohol. A marked increase in both activity and selectivity in the first four reaction runs was observed and this improved performance was preserved in the following catalytic cycles.


Sign in / Sign up

Export Citation Format

Share Document