Manganese-Catalyzed Hydrogen-Autotransfer C−C Bond Formation: α-Alkylation of Ketones with Primary Alcohols

2016 ◽  
Vol 128 (48) ◽  
pp. 15191-15195 ◽  
Author(s):  
Miguel Peña-López ◽  
Patrick Piehl ◽  
Saravanakumar Elangovan ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Bond Formation ◽  
Primary Alcohols ◽  
Hydrogen Autotransfer

Manganese-Catalyzed Hydrogen-Autotransfer C−C Bond Formation: α-Alkylation of Ketones with Primary Alcohols

2016 ◽  
Vol 55 (48) ◽  
pp. 14967-14971 ◽  
Author(s):  
Miguel Peña-López ◽  
Patrick Piehl ◽  
Saravanakumar Elangovan ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Bond Formation ◽  
Primary Alcohols ◽  
Hydrogen Autotransfer

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

2020 ◽  
Vol 85 (18) ◽  
pp. 11952-11958
Author(s):  
Masaki Kobayashi ◽  
Satoshi Itoh ◽  
Keisuke Yoshimura ◽  
Yuya Tsukamoto ◽  
Yasushi Obora
Keyword(s):  
Iridium Complex ◽  
Primary Alcohols ◽  
Hydrogen Autotransfer

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.

Nickel-catalyzed C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy

2020 ◽  
Vol 56 (90) ◽  
pp. 14083-14086
Author(s):  
Peng Yang ◽  
Xiuhua Wang ◽  
Yu Ma ◽  
Yaxin Sun ◽  
Li Zhang ◽  
...  
Keyword(s):  
Primary Alcohols ◽  
Hydrogen Autotransfer ◽  
First Time

A simple catalyst of Ni(OAc)2/P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamides with alcohols for the first time.

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.

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