Ni‐Catalyzed α‐Alkylation of Unactivated Amides and Esters with Alcohols by Hydrogen Auto‐Transfer Strategy DOI
Siba P. Midya, Jagannath Rana,

Jayaraman Pitchaimani

et al.

ChemSusChem, Journal Year: 2018, Volume and Issue: 11(22), P. 3911 - 3916

Published: Oct. 5, 2018

Abstract A transition‐metal‐catalyzed borrowing hydrogen/hydrogen auto‐transfer strategy allows the utilization of feedstock alcohols as an alkylating partner, which avoids formation stoichiometric salt waste and enables a direct benign approach for construction C‐N C−C bonds. In this study, nickel‐catalyzed α‐alkylation unactivated amides ester ( tert ‐butyl acetate) is carried out by using primary under mild conditions. This bond‐forming reaction catalyzed new, molecularly defined nickel(II) NNN‐pincer complex (0.1–1 mol %) proceeds through hydrogen auto‐transfer, thereby releasing water sole byproduct. addition, N ‐alkylation cyclic Ni‐catalytic conditions demonstrated.

Language: Английский

Iron‐Catalyzed Borrowing Hydrogen C‐Alkylation of Oxindoles with Alcohols DOI Creative Commons

Mubarak B. Dambatta,

Kurt Polidano,

Alexander D. Northey

et al.

ChemSusChem, Journal Year: 2019, Volume and Issue: 12(11), P. 2345 - 2349

Published: April 8, 2019

A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited broad reaction scope, allowing benzylic simple primary secondary aliphatic alcohols to be employed as alkylating agents. variety underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50-92 % yield, 79 average yield).

Language: Английский

Citations

65

Manganese‐Catalyzed C−H Olefination Reactions DOI
Yuanyuan Hu, Congyang Wang

ChemCatChem, Journal Year: 2019, Volume and Issue: 11(4), P. 1167 - 1174

Published: Jan. 2, 2019

Abstract Olefins are essential building blocks in organic synthesis, the access to which from simple C−H substrates through catalysis of transition metals, particular earth's abundant ones meets requirements green and sustainable chemistry. Manganese‐catalyzed olefination reactions have emerged as an efficient approach olefins recent years, complementary traditional olefin synthesis. Varieties alkynes, alkenes, allenes well alcohols successfully applied Mn‐catalyzed with substrates, providing multisubstituted bearing varied functional groups. This minireview presents great progresses newly achieved on manganese‐catalyzed reactions.

Language: Английский

Citations

64

Manganese‐Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation DOI

Jannik C. Borghs,

Luis Miguel Azofra, Tobias Biberger

et al.

ChemSusChem, Journal Year: 2018, Volume and Issue: 12(13), P. 3083 - 3088

Published: Dec. 27, 2018

A new base metal catalyzed sustainable multicomponent synthesis of pyrroles from readily available substrates is reported. The developed protocol utilizes an air- and moisture-stable catalyst system enables the replacement themutagenic α-haloketones with abundant 1,2-diols. Moreover, presented method catalytic in sole byproducts this transformation are water hydrogen gas. Experimental computational mechanistic studies indicate that reaction takes place through a combined acceptorless dehydrogenation autotransfer methodology.

Language: Английский

Citations

63

The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst DOI Creative Commons

Christoph Bäumler,

Christof Bauer, Rhett Kempe

et al.

ChemSusChem, Journal Year: 2020, Volume and Issue: 13(12), P. 3110 - 3114

Published: April 21, 2020

Abstract The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis primary amines. use catalysts, especially reusable based on earth‐abundant metals similarly appealing. Here, iron‐catalyzed amines through was realized. A broad scope very good tolerance functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, heterocyclic, as well could be converted smoothly into their corresponding In addition, pharmaceuticals, bioactive compounds, natural products demonstrated. Many groups, such hydroxy, methoxy, dioxol, sulfonyl, boronate ester substituents, tolerated. catalyst easy to handle, selective, dissolved in water employed nitrogen source. key specific Fe complex an N‐doped SiC material support.

Language: Английский

Citations

62

Ni‐Catalyzed α‐Alkylation of Unactivated Amides and Esters with Alcohols by Hydrogen Auto‐Transfer Strategy DOI
Siba P. Midya, Jagannath Rana,

Jayaraman Pitchaimani

et al.

ChemSusChem, Journal Year: 2018, Volume and Issue: 11(22), P. 3911 - 3916

Published: Oct. 5, 2018

Abstract A transition‐metal‐catalyzed borrowing hydrogen/hydrogen auto‐transfer strategy allows the utilization of feedstock alcohols as an alkylating partner, which avoids formation stoichiometric salt waste and enables a direct benign approach for construction C‐N C−C bonds. In this study, nickel‐catalyzed α‐alkylation unactivated amides ester ( tert ‐butyl acetate) is carried out by using primary under mild conditions. This bond‐forming reaction catalyzed new, molecularly defined nickel(II) NNN‐pincer complex (0.1–1 mol %) proceeds through hydrogen auto‐transfer, thereby releasing water sole byproduct. addition, N ‐alkylation cyclic Ni‐catalytic conditions demonstrated.

Language: Английский

Citations

60