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

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidation of secondary and primary alcohols to ketones and carboxylic acids has been developed for the first time.

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RuCl2(DMSO)4 catalyzes the β-alkylation of secondary alcohols with primary alcohols through a hydrogen autotransfer process

Tetrahedron ◽

10.1016/j.tet.2006.07.012 ◽

2006 ◽

Vol 62 (38) ◽

pp. 8982-8987 ◽

Cited By ~ 131

Author(s):

Ricardo Martínez ◽

Diego J. Ramón ◽

Miguel Yus

Keyword(s):

Secondary Alcohols ◽

Primary Alcohols ◽

Hydrogen Autotransfer

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Tungsten-Catalyzed Direct N-Alkylation of Amines with Alcohols

10.26434/chemrxiv.12732047 ◽

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 N-alkylation reaction of amines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)4 (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ 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.

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Tungsten-Catalyzed Direct N-Alkylation of Amines with Alcohols

10.26434/chemrxiv.12732047.v1 ◽

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 N-alkylation reaction of amines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)4 (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ 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.

Download Full-text