Journal ArticleDOI
Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations
Reads0
Chats0
TLDR
In this paper, the authors summarized the advances in the formation of C(sp3)−C(sp 3) bonds between two alkyl electrophiles, with emphasis on the control of chemoselectivity that is exceedingly challenging to achieve due to similar structures and reactivities of two unactivated alkal halides.Abstract:
The formation of C–C bonds directly by catalytic reductive cross-coupling of two different electrophiles represents one of the practical synthetic protocols that differs from the conventional nucleophile/electrophile coupling methods. Particularly the reductive coupling of alkyl electrophiles with other electrophiles is still a challenge. This report summarizes the advances in the formation of C(sp3)–C(sp3) bonds between two alkyl electrophiles, with emphasis on the control of chemoselectivity that is exceedingly challenging to achieve due to similar structures and reactivities of two unactivated alkyl halides. The coupling of alkyl halides with aryl or acyl electrophiles was also discussed based on the chemical approach developed by our group, followed by a brief overview of the reactions of tertiary alkyl halides. In the end, a brief overview of the challenges in this exciting field was illustrated. Whereas the reaction mechanisms generating alkyl–alkyl products are proposed to involve reactions of Ni(I) species with alkyl halides to generate Ralkyl–Ni(III)–Ralkyl intermediates through a radical/Ni cage-rebound process, the obtained evidence seemingly supports that the radical chain mechanism governs the acylation and arylation of alkyl halides. The latter features a cage-escaped alkyl radical.read more
Citations
More filters
Journal ArticleDOI
Transition-Metal-Catalyzed Carboxylation Reactions with Carbon Dioxide.
TL;DR: It is indicated that catalytic carboxylation reactions have entered a new era of exponential growth, evolving into a mature discipline that allows for streamlining the synthesis of carboxylic acids, building blocks of utmost relevance in industrial endeavors.
Journal ArticleDOI
Transition-Metal (Cu, Pd, Ni)-Catalyzed Difluoroalkylation via Cross-Coupling with Difluoroalkyl Halides.
TL;DR: Major efforts are summarized on copper-, palladium-, and nickel-catalyzed difluoroalkylations of aromatics with low-cost and widely available difLUroalkyl halides as fluoroALKyl sources for transition-metal-catalystzed d ifluoroalksylation reactions via cross-coupling.
Journal ArticleDOI
Metal-Catalyzed Carboxylation of Organic (Pseudo)halides with CO2
TL;DR: This perspective describes the evolution of metal-catalyzed reductive carboxylation of organic (pseudo)halides from its inception in the pioneering stoichiometric work of Osakada to the present, and anticipates that these processes might fall into more than one distinct mechanistic category depending on the substrate utilized.
Journal ArticleDOI
Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.
TL;DR: In this Perspective, the progress that has been made toward Ni-catalyzed enantioselective reductive cross-coupling reactions is summarized.
Journal ArticleDOI
Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes.
TL;DR: An intermolecular, three-component reductive dicarbofunctionalization of alkenes is presented here and the combination of Ni catalysis with TDAE as final reductant enables the direct formation of Csp3-Csp3 and Csp 3-CSP2 bonds across a variety of π-systems.
References
More filters
Journal ArticleDOI
Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.
Journal ArticleDOI
Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides
Zhiwei Zuo,Derek T. Ahneman,Lingling Chu,Jack A. Terrett,Abigail G. Doyle,David W. C. MacMillan +5 more
TL;DR: In this article, the synergistic combination of photoredox catalysis and nickel catalysis was used to achieve a direct decarboxylative sp(3)-sp(2) cross-coupling of amino acids with aryl halides.
Journal ArticleDOI
Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
TL;DR: A mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns.
Journal ArticleDOI
Catalysts for Cross‐Coupling Reactions with Non‐activated Alkyl Halides
Anja C. Frisch,Matthias Beller +1 more
TL;DR: This Minireview highlights selected examples of metal-catalyzed coupling methods and is intended to encourage chemists to exploit the potential of these approaches in organic synthesis.