Manganese Catalyzed α-Alkylation of Nitriles with Primary Alcohols

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(10), P. 9226 - 9231

Published: Aug. 24, 2018

The manganese(I) complex bearing a bidentate hydrazone ligand efficiently catalyzes the α-alkylations of nitrile using primary alcohols as alkylating agents. α-Functionalized nitriles were selectively obtained in good to excellent yields. reaction is environmentally benign, producing water sole byproduct. Both benzylic and aliphatic could be used functional groups tolerated.

Language: Английский

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Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex

Organic Letters, Journal Year: 2019, Volume and Issue: 21(9), P. 3223 - 3227

Published: April 22, 2019

A sustainable synthesis of quinazoline and 2-aminoquinoline via acceptorless dehydrogenative annulation is presented. The reaction catalyzed by earth-abundant well-defined manganese complexes bearing NNS ligands. Furthermore, a one-pot synthetic strategy for the 2-alkylaminoquinolines through sequential N-alkylation has also been demonstrated.

Language: Английский

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Manganese‐Catalyzed Direct Olefination of Methyl‐Substituted Heteroarenes with Primary Alcohols

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(29), P. 9126 - 9130

Published: May 28, 2018

Abstract Herein, we present the first catalytic direct olefination of methyl‐substituted heteroarenes with primary alcohols through an acceptorless dehydrogenative coupling. The reaction is catalyzed by a complex earth‐abundant transition metal manganese that stabilized bench‐stable NNN pincer ligand derived from 2‐hydrazinylpyridine. environmentally benign, producing only hydrogen and water as byproducts. A large number E ‐disubstituted olefins were selectively obtained high efficiency.

Language: Английский

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Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions

ChemCatChem, Journal Year: 2019, Volume and Issue: 12(7), P. 1891 - 1902

Published: Dec. 21, 2019

Abstract Acceptorless dehydrogenative coupling (ADC) has emerged as a powerful tool in the chemists’ arsenal for construction of various carbon‐carbon and carbon‐heteroatom bonds. These protocols are highly atom economical environmentally benign they do not require pre‐functionalized starting material produce only dihydrogen (and water) by‐product. This technique, coupled with Earths’ abundant less toxic manganese catalysis, can prove to be vital strategy generation molecular complexity from simple materials. Manganese catalyzed DHC been growing interest, low‐ high‐valent catalysts have developed. were demonstrated show excellent catalytic activity formation carbon‐carbon, bonds, cascade reactions. In this mini‐review, we would like highlight recent progress that made ADC

Language: Английский

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Phosphine-Free Well-Defined Mn(I) Complex-Catalyzed Synthesis of Amine, Imine, and 2,3-Dihydro-1H-perimidine via Hydrogen Autotransfer or Acceptorless Dehydrogenative Coupling of Amine and Alcohol

Organometallics, Journal Year: 2019, Volume and Issue: 38(8), P. 1815 - 1825

Published: April 12, 2019

The application of nontoxic, earth-abundant transition metals in place costly noble is a paramount goal catalysis and especially interesting if the air- moisture-stable ligand scaffold used. Herein, we report synthesis amines/imines directly from alcohol amines via hydrogen autotransfer or acceptorless dehydrogenation catalyzed by well-defined phosphine-free Mn complexes. Both imines can be obtained same set alcohols using catalyst, only tuning reaction conditions. amount nature base are found to highly important aspect for observed selectivity. primary secondary have been employed as substrates N-alkylation reaction. As highlight, showed chemoselective resveratrol derivatives. Furthermore, Mn-catalyzed dehydrogenative structurally 2,3-dihydro-1H-perimidines has also demonstrated. Density functional theory calculations were carried out model path calculate profile.

Language: Английский

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