scholarly journals Cobalt-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols via Borrowing Hydrogen/Hydrogen Autotransfer

2017 ◽  
Vol 23 (50) ◽  
pp. 12110-12113 ◽  
Author(s):  
Frederik Freitag ◽  
Torsten Irrgang ◽  
Rhett Kempe
Keyword(s):  
Secondary Alcohols ◽  
Primary Alcohols ◽  
Borrowing Hydrogen ◽  
Hydrogen Autotransfer

Iridium–CNP complex catalyzed cross-coupling of primary alcohols and secondary alcohols by a borrowing hydrogen strategy

RSC Advances ◽  
2014 ◽  
Vol 4 (81) ◽  
pp. 42924-42929 ◽  
Author(s):  
Dawei Wang ◽  
Keyan Zhao ◽  
Xin Yu ◽  
Hongyan Miao ◽  
Yuqiang Ding
Keyword(s):  
Cross Coupling ◽  
Secondary Alcohols ◽  
Primary Alcohols ◽  
Borrowing Hydrogen

scholarly journals Tungsten-Catalyzed Direct N-Alkylation of Amines with Alcohols

2020 ◽  
Author(s):  
Xiao-Bing Lan ◽  
Zongren Ye ◽  
Weikang Li ◽  
Jiahao Liu ◽  
Ming Huang ◽  
...  
Keyword(s):  
Homogeneous Catalysis ◽  
Alkylation Reaction ◽  
Synthetic Method ◽  
Computational Studies ◽  
Primary Alcohols ◽  
Major Goal ◽  
Earth Abundant ◽  
Borrowing Hydrogen ◽  
Hydrogen Autotransfer

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.

scholarly journals Tungsten-Catalyzed Direct N-Alkylation of Amines with Alcohols

2020 ◽  
Author(s):  
Xiao-Bing Lan ◽  
Zongren Ye ◽  
Weikang Li ◽  
Jiahao Liu ◽  
Ming Huang ◽  
...  
Keyword(s):  
Homogeneous Catalysis ◽  
Alkylation Reaction ◽  
Synthetic Method ◽  
Computational Studies ◽  
Primary Alcohols ◽  
Major Goal ◽  
Earth Abundant ◽  
Borrowing Hydrogen ◽  
Hydrogen Autotransfer

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.

Bifunctional Ru(ii) complex catalysed carbon–carbon bond formation: an eco-friendly hydrogen borrowing strategy

2016 ◽  
Vol 14 (46) ◽  
pp. 10988-10997 ◽  
Author(s):  
Kaushik Chakrabarti ◽  
Bhaskar Paul ◽  
Milan Maji ◽  
Bivas Chandra Roy ◽  
Sujan Shee ◽  
...  
Keyword(s):  
Bond Formation ◽  
Secondary Alcohols ◽  
Primary Alcohols ◽  
One Pot ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Borrowing Hydrogen

Bifunctional Ru(ii) complex (0.1 mol%) catalysed one-pot β-alkylation of secondary alcohols with primary alcohols and double alkylation of cyclopentanol were carried out successfully following the atom economical borrowing hydrogen methodology.

ChemInform Abstract: Iridium-CNP Complex Catalyzed Cross-Coupling of Primary Alcohols and Secondary Alcohols by a Borrowing Hydrogen Strategy.

ChemInform ◽  
2015 ◽  
Vol 46 (13) ◽  
pp. no-no
Author(s):  
Dawei Wang ◽  
Keyan Zhao ◽  
Xin Yu ◽  
Hongyan Miao ◽  
Yuqiang Ding
Keyword(s):  
Cross Coupling ◽  
Secondary Alcohols ◽  
Primary Alcohols ◽  
Borrowing Hydrogen

scholarly journals C‐Alkylation of Secondary Alcohols by Primary Alcohols through Manganese‐Catalyzed Double Hydrogen Autotransfer

ChemSusChem ◽  
2018 ◽  
Vol 12 (13) ◽  
pp. 3099-3102 ◽  
Author(s):  
Osama El‐Sepelgy ◽  
Esteban Matador ◽  
Aleksandra Brzozowska ◽  
Magnus Rueping
Keyword(s):  
Secondary Alcohols ◽  
Primary Alcohols ◽  
Hydrogen Autotransfer ◽  
Double Hydrogen

Ruthenium(II) Complexes with N-Heterocyclic Carbene-Phosphine Ligands for the N-Alkylation of Amines with Alcohols

2021 ◽  
Author(s):  
Ming Huang ◽  
Yinwu Li ◽  
Xiao-Bing Lan ◽  
Jiahao Liu ◽  
Cunyuan Zhao ◽  
...  
Keyword(s):  
Metal Hydride ◽  
Phosphine Ligands ◽  
Hydride Complexes ◽  
Borrowing Hydrogen ◽  
Hydrogen Autotransfer

Metal hydride complexes are key intermediates for N-alkylation of amines with alcohols by borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols...

Revisiting Sodium Hypochlorite Pentahydrate (NaOCl·5H2O) for the Oxidation of Alcohols in Acetonitrile without Nitroxyl Radicals

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2404-2407 ◽  
Author(s):  
Tsunehisa Hirashita ◽  
Yuto Sugihara ◽  
Shota Ishikawa ◽  
Yohei Naito ◽  
Yuta Matsukawa ◽  
...  
Keyword(s):  
Sodium Hypochlorite ◽  
Nitroxyl Radicals ◽  
Secondary Alcohols ◽  
Primary Alcohols ◽  
Oxidation Of Alcohols

Sodium hypochlorite pentahydrate (NaOCl·5H2O) is capable of oxidizing alcohols in acetonitrile at 20 °C without the use of catalysts. The oxidation is selective to allylic, benzylic, and secondary alcohols. ­Aliphatic primary alcohols are not oxidized.

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