Rhodium(<scp>iii</scp>)-catalyzed olefinic C–H alkynylation of enamides at room temperature

Feng, Chao; Feng, Donghai; Loh, Teck‐Peng

doi:10.1039/c4cc04072d

Cited by 146 publications

(63 citation statements)

References 53 publications

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“…Loh and co-workers extended the rhodium-catalyzed alkynylation of olefins to both acrylamides and enamides. [62] Loh and co-workers, as well as Zhu and co-workers independently reported the rhodiumcatalyzed C7-alkynylation of indolines, whereas Li and Zhou and co-workers used an iridium catalyst for the same transformation. [63] Chang and co-workers developed an efficient C8-alkynylation of quinoline-N-oxide using a cationic rhodium catalyst.…”

Section: Reviewmentioning

confidence: 99%

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

et al. 2016

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Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their potential for functional‐group transfer has only begun to be investigated recently. The use of benziodoxol(on)es for trifluoromethylation (Togni's reagents) is already widely recognized, but other transformations have also attracted strong interest recently. In this Review, the development in the area since 2011 will be presented. After a short summary of synthetic methods to prepare benziodoxol(on)e reagents, their use to construct carbon–heteroatom and carbon–carbon bonds will be presented. In particular, the introduction of alkynes by using ethynylbenziodoxol(on)e (EBX) reagents has been highly successful. Breakthroughs in the introduction of alkoxy, azido, difluoromethyl, and cyano groups will also be described.

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Section: Reviewmentioning

confidence: 99%

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

et al. 2016

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“…With these three reports, the basis was set for a broader use of EBX reagents in rhodium catalysis. Loh and co-workers continued their work and reported the alkynylation of acryl tosyl imides and enamides [132][133]. The reaction with acryl 23 imides proceeded also with disubstituted alkenes and allowed to extend the scope of this transformation.…”

Section: Alkynylation Of Aromatic and Vinylic C-h Bondsmentioning

confidence: 95%

Alkynylation with Hypervalent Iodine Reagents

Waser

2015

Topics in Current Chemistry

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Alkynes are among the most versatile functional groups in organic synthesis. They are also frequently used in chemical biology and materials science. Whereas alkynes are traditionally added as nucleophiles into organic molecules, hypervalent iodine reagents offer a unique opportunity for the development of electrophilic alkyne synthons. Since 1985, alkynyliodonium salts have been intensively used for the alkynylation of nucleophiles, in particular soft carbon nucleophiles and heteroatoms. They have made especially a strong impact in the synthesis of highly useful ynamides. Nevertheless, their use has been limited by their instability. Since 2009, more stable ethynylbenziodoxol(on)e (EBX) reagents have been discovered as superior electrophilic alkyne synthons in many transformations. They can be used for the alkynylation of acidic C-H bonds with bases or aromatic C-H bonds using transition metal catalysts. They were also highly successful for the functionalization of radicals or transition metal-catalyzed domino processes. Finally, they allowed the alkynylation of a further range of heteroatom nucleophiles, especially thiols, under exceptionally mild conditions. With these recent discoveries, hypervalent iodine reagents have definitively demonstrated their utility for the efficient synthesis of alkynes based on non-classical disconnections.

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“…Presumably due to the weakly coordinating ability of Ts-imide group, the highly reactive ligated catalyst can be formed to react with the substrates. Furthermore, some cyclic or acylic ,-disubstituted acrylamide derivatives are all compatible by switching the solvents, which shows potential applications in 1,3-enynes synthesis (Scheme 6) [7].…”

Section: Csp -Csp Bond Formation Through Directed Vinylic C-h Bond Acmentioning

confidence: 99%

Directing group-assisted transition-metal-catalyzed vinylic C-H bond functionalization

et al. 2015

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Rhodium(iii)-catalyzed olefinic C–H alkynylation of enamides at room temperature

Cited by 146 publications

References 53 publications

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

Alkynylation with Hypervalent Iodine Reagents

Directing group-assisted transition-metal-catalyzed vinylic C-H bond functionalization

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