Journal ArticleDOI
Direct Difluoromethylation of Aryl Halides via Base Metal Catalysis at Room Temperature.
Long Xu,David A. Vicic +1 more
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TLDR
This new zinc reagent is a free-flowing solid that can be used in combination with a nickel catalyst to difluoromethylate aryl iodides, bromides, and triflates at room temperature.Abstract:
A stable and isolable difluoromethyl zinc reagent has been prepared through the reaction of ICF2H with diethyl zinc and DMPU. This new zinc reagent is a free-flowing solid and can be used in combination with a nickel catalyst to difluoromethylate aryl iodides, bromides, and triflates at room temperature. Such mild conditions for the catalytic difluoromethylation of these substrates are unprecedented.read more
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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
Key Green Chemistry research areas from a pharmaceutical manufacturers’ perspective revisited
Marian C. Bryan,Peter J. Dunn,David Entwistle,Fabrice Gallou,Stefan G. Koenig,John D. Hayler,Matthew R. Hickey,Shaun Hughes,Michael E. Kopach,Gerard Moine,Paul G. Richardson,Frank Roschangar,Alan Steven,Franz J. Weiberth +13 more
TL;DR: In 2007, the members of the ACS Green Chemistry Institute® Pharmaceutical Roundtable assembled a list of key green chemistry research areas to both identify transformations that would benefit from improvements in process greenness and to encourage academic research to this end as mentioned in this paper.
Journal ArticleDOI
Difluoromethylation Reactions of Organic Compounds.
TL;DR: Three main methodological protocols will be presented in this review article for the late-stage introduction of a CF2 H or CF2 Y moieties into organic substrates: a metal-photoredox catalysis, through transition metal-catalyzed thermal protocols, and from transition-metal-free strategies.
Journal ArticleDOI
Metal-Catalyzed Direct Difluoromethylation Reactions
Jian Rong,Chuanfa Ni,Jinbo Hu +2 more
TL;DR: In this article, a focus review summarizes recent developments in metal-catalyzed direct difluoromethylation reactions, including CF2H and CF3H.
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Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel
TL;DR: A nickel-catalyzed three-component reaction for the synthesis of difluoroalkylated compounds through tandem dif LUalkylation-arylation of enamides has been developed, showing the low-cost nickel catalyst, synthetic convenience, excellent functional-group compatibility and high reaction efficiency.
References
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Journal ArticleDOI
A New Reagent for Direct Difluoromethylation
Yuta Fujiwara,Janice A. Dixon,Rodrigo A. Rodriguez,Ryan D. Baxter,Darryl D. Dixon,Michael R. Collins,Donna G. Blackmond,Phil S. Baran +7 more
TL;DR: This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated π-systems and thiols.
Journal ArticleDOI
Copper-Mediated Difluoromethylation of Aryl and Vinyl Iodides
Patrick S. Fier,John F. Hartwig +1 more
TL;DR: The reaction of electron-neutral, electron-rich, and sterically hindered aryl and vinyl iodides with the combination of CuI, CsF and TMSCF(2)H leads to the formation of difluoromethyl-substituted products in high yield with good functional group compatibility.
Journal ArticleDOI
Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides
TL;DR: The results and studies with an organic reductant (TDAE) argue against the intermediacy of organozinc reagents.
Journal ArticleDOI
A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.
TL;DR: A new methodology for aromatic difluoromethylation is described and it is shown that Aryl iodides reacted with α-silyldifluoroacetates upon treatment with copper catalyst in DMSO or DME to give the corresponding aryldif LUacetates in moderate to good yields.
Journal ArticleDOI
Copper-mediated difluoromethylation of (hetero)aryl iodides and β-styryl halides with tributyl(difluoromethyl)stannane.
G. K. Surya Prakash,Somesh K. Ganesh,John-Paul Jones,Aditya Kulkarni,Kamil Masood,Joseph K. Swabeck,George A. Olah +6 more
TL;DR: The synthesis of tributyl(difloromethyl)stannane and its application in the copper-mediated difluorometHylation of iodoarenes and b-styryl halides is reported and requires a significant excess of TMSCF2H.