Recent applications of gallium and gallium halides as reagents in organic synthesis

Gupta, Manoj K.; O’Sullivan, Timothy P.

doi:10.1039/c3ra42316f

Cited by 27 publications

(16 citation statements)

References 102 publications

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“…Owing to the ability of Ga(III) complexes to catalyze hydroarylation of alkynes to give phenyl‐substituted alkenes,28 a formal three‐component coupling between 4‐ethynylbiphenyl, anisole, and H 2 was attempted (Scheme ). Gratifyingly, the expected product 7 was isolated in 78 % yield.…”

Section: Resultsmentioning

confidence: 99%

Gallium‐Assisted Transfer Hydrogenation of Alkenes

Michelet

Bour

Gandon

2014

Chemistry A European J

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Section: Resultsmentioning

confidence: 99%

Gallium‐Assisted Transfer Hydrogenation of Alkenes

Michelet

Bour

Gandon

2014

Chemistry A European J

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“…However, a weak LA failed to catalyze the reaction (entry 4), while standard LAs also afforded the substitution product 4aa (entries 5–6). Gratifyingly, in the presence of GaBr 3 with stronger acidity, the dearomative 3,3′-bisindole product 3aa was obtained (entry 7). These results revealed that the acidity of the catalysts imposed some effect on the reaction, since standard acidic conditions could only facilitate the production of the substitutive product 4aa , while GaBr 3 , which is a stronger LA, could promote the formation of the dearomatized product 3aa .…”

Section: Resultsmentioning

confidence: 99%

Gallium Bromide-Promoted Dearomative Indole Insertion in 3-Indolylmethanols: Chemoselective and (Z/E)-Selective Synthesis of 3,3′-Bisindole Derivatives

et al. 2016

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Gallium bromide (GaBr)-promoted dearomative indole insertion in 3-indolylmethanols has been established, which chemoselectively constructs a biologically important 3,3'-bisindole framework bearing an all-carbon quaternary center in high yields and excellent (Z)-selectivities (up to 99% yield, all >95:5 Z/E). The reaction pathway was suggested to include a tandem sequence of Michael addition/C-C bond cleavage/nucleophilic addition, wherein the strong acidity of GaBr played a crucial role in the key step of C-C bond cleavage. This reaction not only provides a new strategy for dearomatization of indoles, but also represents a new reaction category for 3-indolylmethanols, which involves a rarely reported late-stage C-C bond cleavage of 3-indolylmethanol derivatives. In addition, this approach also offers an efficient method for the synthesis of biologically important 3,3'-bisindole derivatives.

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“…[ 11,13 ] Additionally, Ga is an oxophilic metal which exists in several oxidation states; Ga(0), Ga(I), and Ga(III), and has the ambiphilic catalytic behavior necessary for C–C bond formation. [ 16,20,21 ]…”

Section: Figurementioning

confidence: 99%

Liquid‐Metal‐Templated Synthesis of 2D Graphitic Materials at Room Temperature

Mayyas

Kumar

et al. 2020

Advanced Materials

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Room‐temperature synthesis of 2D graphitic materials (2D‐GMs) remains an elusive aim, especially with electrochemical means. Here, it is shown that liquid metals render this possible as they offer catalytic activity and an ultrasmooth templating interface that promotes Frank–van der Merwe regime growth, while allowing facile exfoliation due to the absence of interfacial forces as a nonpolar liquid. The 2D‐GMs are formed at low onset potential and can be in situ doped depending on the choice of organic precursors and the electrochemical set‐up. The materials are tuned to exhibit porous or pinhole‐free morphologies and are engineered for their degree of oxidation and number of layers. The proposed liquid‐metal‐based room‐temperature electrochemical route can be expanded to many other 2D materials.

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Recent applications of gallium and gallium halides as reagents in organic synthesis

Cited by 27 publications

References 102 publications

Gallium‐Assisted Transfer Hydrogenation of Alkenes

Gallium‐Assisted Transfer Hydrogenation of Alkenes

Gallium Bromide-Promoted Dearomative Indole Insertion in 3-Indolylmethanols: Chemoselective and (Z/E)-Selective Synthesis of 3,3′-Bisindole Derivatives

Liquid‐Metal‐Templated Synthesis of 2D Graphitic Materials at Room Temperature

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