Copper‐Catalyzed Three‐Component Reactions of 2‐Iodo‐2,2‐difluoroacetophenones, Alkynes, and Trimethylsilyl Cyanide

Wu, Pingjie; Zheng, Cheng; Wang, Xia; Wu, Fanhong

doi:10.1002/ejoc.202001650

Cited by 15 publications

(6 citation statements)

References 61 publications

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“…As we know, organonitriles can be used as important bioactive molecular, [15] as well as useful synthons for the preparation of ketones, carboxylic acids, and amides, etc [16] . Recently, we have reported a copper‐catalyzed reaction of 2‐iodo‐2,2‐difluoroacetophenones, alkyne and trimethylsilyl cyanide (TMSCN) to provide a facile method for the synthesis of difluoroacyl‐substituted nitriles [16c] . Hence, in this work, we turned to explore the three‐component reaction of α‐halo‐α‐fluoroketones with styrene and TMSCN under Copper‐catalyzed reaction condition.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Application of Monofluoroalkyl Building Blocks: α‐Halo‐α‐fluoroketones

Zheng

Cui

et al. 2022

Eur J Org Chem

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A convenient and versatile synthesis of α‐halo‐α‐fluoroketones, including α‐iodo‐α‐fluoroketones, α‐bromo‐α‐fluoroketones and α‐chloro‐α‐fluoroketones by using Wu–Colby's protocol involving the release of trifluoroacetate was reported. The ketones’ application as monofluoroalkyl building blocks was explored through coupling and radical reactions. The results indicated that α‐iodo‐α‐fluoroketones are the most popular reagents to construct diverse valuable single‐fluorinated molecules.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Application of Monofluoroalkyl Building Blocks: α‐Halo‐α‐fluoroketones

Zheng

Cui

et al. 2022

Eur J Org Chem

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“…Mechanistic insight, including DFT calculations, revealed involvement of a (isocyano)Cu(II)/Cu(I) catalytic cycle rather than cyanoCu(III) species and rationalized the high diastereoselectivity controlled by a remote stereogenic centre. Recently, Wu utilized a similar catalyst system for cyanofluoroalkylation of alkynes with iododfluoromethyl ketones [205] . Shortly after, the enantioselective variant of the transformation was disclosed utilizing low loading of a Cu−bisoxazoline complex and benzoylperoxide [206] .…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

Fluoroalkyl Iodides in Fluoroalkylative Difunctionalization of C−C Multiple Bonds

Lucio‐Martínez

Chaładaj

2023

Adv Synth Catal

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Fluorinated alkyl iodides serve as a convenient and inexpensive source of fluoroalkyl radicals that can readily undergo addition to the CÀ C unsaturated bonds of alkynes and alkenes which is the foundation for a variety of useful synthetic protocols. Since 2010 this field has witnessed huge progress in several respects. First the portfolio of fluorinated alkyl iodides was extended beyond only simple perfluoroalkyl iodides (C n F 2n + 1 I). In particular, employment of iododifluoroÀ methyl-carbonyls and phosphonates has enabled facile installation of the medicinally relevant difluoromethylene motif. Secondly, from a conceptual point of view, novel strategies for activation of fluoroalkyl iodides towards radical formation have been introduced, relying on the formation of electron donor-acceptor (EDA) complexes, photoredox catalysis, frustrated Lewis pairs and transition metal catalysis, complementing prior approaches based on heat and UV induced CÀ I homolysis, radical initiators, and simple electron transfer processes. Based on these strategies a range of novel fluoroalkylative transformations of unsaturated systems have been added to classical iodoperfluoroalkylation. Broadly applicable protocols for simple fluoroalkylation and hydrofluoroalkylation, as well as for more sophisticated, complexitybuilding methods of fluoroalkylation-annulation and tandem multicomponent fluoroalkylations with concomitant installation of another functionality have been recently disclosed. This review summarizes the progress achieved since 2010 in the reactivity of fluoroalkyl iodides towards alkenes and alkynes with emphasis placed on the above-mentioned advances.1.

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“…Cu(I) catalyzed the three component reaction of 2-iodo-2,2-difluoroacetophenone, acetynes and TMSCN, which was presented by Wu’s group ( Scheme 24 ) [ 77 ]. This reaction provides a simple strategy for the synthesis of difluoroacyl-substituted nitriles, which may be a potentially useful fluoro-organic intermediate for further conversion in drug discovery.…”

Section: Difluoroalkylation–multicomponent Reactionsmentioning

confidence: 99%

Copper-Catalyzed Difluoroalkylation Reaction

et al. 2022

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Copper‐Catalyzed Three‐Component Reactions of 2‐Iodo‐2,2‐difluoroacetophenones, Alkynes, and Trimethylsilyl Cyanide

Cited by 15 publications

References 61 publications

Synthesis and Application of Monofluoroalkyl Building Blocks: α‐Halo‐α‐fluoroketones

Synthesis and Application of Monofluoroalkyl Building Blocks: α‐Halo‐α‐fluoroketones

Fluoroalkyl Iodides in Fluoroalkylative Difunctionalization of C−C Multiple Bonds

Copper-Catalyzed Difluoroalkylation Reaction

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