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Alkylation

About: Alkylation is a research topic. Over the lifetime, 29915 publications have been published within this topic receiving 464944 citations. The topic is also known as: alkylation reaction.


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TL;DR: A ligand-controlled and site-selective nickel catalyzed Suzuki-Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed, providing a facile route for C(sp2)-C(sp3) bond formation in a straightforward fashion by successful suppression of the undesired β-hydride elimination process.
Abstract: A ligand-controlled and site-selective nickel catalyzed Suzuki–Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed. This methodology provides a facile route for C(sp2)–C(sp3) bond formation in a straightforward fashion by successful suppression of the undesired β-hydride elimination process. By simply switching the phosphorus ligand, the ester substrates are converted into the alkylated arenes and ketone products, respectively. The utility of this newly developed protocol was demonstrated by its wide substrate scope, broad functional group tolerance and application in the synthesis of key intermediates for the synthesis of bioactive compounds. DFT studies on the oxidative addition step helped rationalizing this intriguing reaction chemoselectivity: whereas nickel complexes with bidentate ligands favor the C(aryl)–C bond cleavage in the oxidative addition step leading to the alkylated product via a decarbonylative process, nickel complexes ...

127 citations

Journal ArticleDOI

127 citations

Journal ArticleDOI
TL;DR: A visible-light-driven Minisci protocol that employs an inexpensive earth-abundant metal catalyst, decacarbonyldimanganese Mn2 (CO)10 , to generateAlkyl radicals from alkyl iodides has been developed and is demonstrated on the late-stage functionalization of complex nitrogen-containing drugs.
Abstract: A visible-light-driven Minisci protocol that employs an inexpensive earth-abundant metal catalyst, decacarbonyldimanganese Mn2 (CO)10 , to generate alkyl radicals from alkyl iodides has been developed. This Minisci protocol is compatible with a wide array of sensitive functional groups, including oxetanes, sugar moieties, azetidines, tert-butyl carbamates (Boc-group), cyclobutanes, and spirocycles. The robustness of this protocol is demonstrated on the late-stage functionalization of complex nitrogen-containing drugs. Photophysical and DFT studies indicate a light-initiated chain reaction mechanism propagated by . Mn(CO)5 . The rate-limiting step is the iodine abstraction from an alkyl iodide by . Mn(CO)5 .

127 citations

Journal ArticleDOI
TL;DR: In this paper, a variety of aromatic and heteroaromatic amines were selectively converted into the corresponding secondary amines in moderate to excellent yields without any co-catalysts such as bases and stabilizing ligands.

126 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023652
20221,161
2021561
2020516
2019630
2018631