Recent advances of propiolic acids in organic reactions

Chen, Chuanli; Wu, Jinjing; Yan, Guobing; Huang, Dayun

doi:10.1016/j.tetlet.2019.151415

Cited by 22 publications

(11 citation statements)

References 221 publications

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“…Radical additions to the alkynes like propiolic acids, ethynylbenziodoxolones or haloalkynes, could provide alkynyl sulfones by releasing CO 2 , HX or 2‐iodobenzoic acid (Eq. 34‐1).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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“…Radical additions to the alkynes like propiolic acids, ethynylbenziodoxolones or haloalkynes, could provide alkynyl sulfones by releasing CO 2 , HX or 2‐iodobenzoic acid (Eq. 34‐1).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…Especially, substituted alkenes could be efficiently obtained by an addition‐decarboxylation strategy. As both propiolic acids and ynones have similar structure with cinnamic acids, which contain electrophilic unsaturated bonds and electron‐withdrawing groups. Hence, our previous review can be used as a reference for the radical and Michael addition.…”

Section: Discussionmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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“…As to the decarboxylation of propiolic acid, these studies clearly show that the activation energy is highly condition-dependent. The rich chemistry of propiolic acids has been reviewed and classified into five categories . Among them, copper-based catalysts play an important role in the cases of the alkyne or acid component as an electrophile and decarboxylative coupling.…”

Section: Introductionmentioning

confidence: 99%

Propiolic Acid on Cu(100) and Oxygen-Precovered Cu(100): Multiple Adsorption States and Diversified Reaction Routes

Lin

et al. 2023

J. Phys. Chem. C

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Multiple adsorption geometries and diversified reaction pathways of the bifunctional propiolic acid (HC�C−COOH) on Cu(100) and oxygen-covered Cu(100) (O/Cu(100)) have been investigated, using the surface analytical techniques of X-ray photoelectron spectroscopy, reflection−absorption infrared spectroscopy, and temperatureprogrammed reaction/desorption, with the assistance of density functional theory calculations. Upon adsorption on O/Cu(100) at 105 K, the deprotonation occurs promptly to form perpendicular HC�C−COO (propiolate) with the COO attaching to the surface. Decomposition of this intermediate results in the loss of CO and CO 2 at ∼230 K and formation of the plausible surface intermediates of CCCOOH, tilted HCCCOO, and CCH. The first two are derived from rearrangement or geometric transformation of the perpendicular HC�C−COO. CCH is the precursor for the C 2 H 2 desorption at ∼335 K. C 2 (acetylide) and >C�C�O (ketenylidene) exist on the surface at higher temperatures and are responsible for the desorption of CO and CO 2 at 580 K. On Cu(100), adsorption of propiolic acid at 105 K generates tilted HCCCOOH and HCCCOO, via the HCC group bonding to the surface. Perpendicular HC�C−COO is an additional species found at a higher coverage. Hydrogenation of the HCCCOO occurs, possibly involving the surface species of CHCHCOO and CH 2 CCOO. H 2 , H 2 O, CO, and CO 2 evolve from decomposition of these carboxylates at ∼315 K, also forming perpendicular CH 2 �CHCOO and >C�C�O. Adsorbed CH 3 CH 2 COO can be produced at a higher coverage. In addition, C 2 H 2 and C 2 H 4 desorb at ∼360 K. Decomposition of the perpendicular CH 2 �CHCOO, >C�C�O, and CH 3 CH 2 COO is responsible for the products of H 2 , CO, CO 2 , and C 6 H 6 found at ∼550 K.

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Recent advances of propiolic acids in organic reactions

Cited by 22 publications

References 221 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Recent Advances of Cinnamic Acids in Organic Synthesis

Propiolic Acid on Cu(100) and Oxygen-Precovered Cu(100): Multiple Adsorption States and Diversified Reaction Routes

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