ChemInform Abstract: Multicomponent Hetero‐[4 + 2] Cycloaddition/Allylboration Reaction: From Natural Product Synthesis to Drug Discovery

Hall, Dennis G.; Rybak, Taras; Verdelet, Tristan

doi:10.1002/chin.201652489

Cited by 2 publications

(2 citation statements)

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“…23 C−C cycloaddition is important in synthetic chemistry, facilitating modular accesses to the synthesis of natural products, 24,25 agrochemicals, 26 and pharmaceuticals. 27,28 Among the cycloaddition reactions, the DA reaction between a diene and a dienophile is well-known for its regioselectivity and stereoselectivity. DA reactions usually require catalysts such as Lewis acids, 29,30 alkali cations, 31 and enzymes.…”

Section: Introductionmentioning

confidence: 99%

Designer “Quasi-Benzyne”: The Spontaneous Reduction of Ortho-Diiodotetrafluorobenzene on Water Microdroplets

Chen,

Wang,

Chiba

et al. 2024

J. Am. Chem. Soc.

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It has been widely shown that water microdroplets have a plethora of unique properties that are highly distinct from those of bulk water, among which an especially intriguing one is the strong reducing power as a result of the electrons spontaneously generated at the air−water interface. In this study, we take advantage of the reducing power of water microdroplets to reduce ortho-diiodotetrafluorobenzene (o-C 6 F 4 I 2 ) into a C 6 F 4 I 2 •− radical anion. Photoelectron spectroscopy and density functional theory computations reveal that the excess electron in C 6 F 4 I 2 •− occupies the I−C1−C2−I linkage, which elongates the C−I bonds but surprisingly shortens the C1−C2 bond, making the bond order higher than a double bond, similar to the benzyne molecule, so we named it "quasi-benzyne". The C 6 F 4 I 2•− anion was further successfully utilized in a Diels−Alder reaction, a typical reaction for benzyne. This study provides a good example of strategically utilizing the spontaneous properties of water microdroplets and generating an especially exotic anion, and we anticipate that microdroplet chemistry can be an avenue rich in opportunities for new catalyst-free organic reactions.

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Section: Introductionmentioning

confidence: 99%

Designer “Quasi-Benzyne”: The Spontaneous Reduction of Ortho-Diiodotetrafluorobenzene on Water Microdroplets

Chen,

Wang,

Chiba

et al. 2024

J. Am. Chem. Soc.

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“…A. Strecker reported the first MCR in 1850, using a multicomponent approach to synthesize α-amino acids 17 . After that, several reports evolved MCRs, including the total synthesis of biologically active natural products and drug molecules 18 .…”

Section: Introductionmentioning

confidence: 99%

One pot synthesis of some novel indole derivatives and their antimicrobial activity

et al. 2023

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<p>In this study, we describe the creation of a straightforward and incredibly effective protocol for the synthesis of new 3-Substituted indole derivatives. This multicomponent reaction involved indole, acetylacetone and active aldehyde derivatives in the presence of ethanol as solvent followed by acetonitrile as a base. We go through current developments in organic synthesis methodology for multicomponent reactions that produce substituted indole derivatives with a more environmentally friendly base catalytic condition, as well as the applications that go along with them. FT-IR, 1H-NMR and MS are used to characterise the synthesized compound of indole derivatives. Antibacterial activity of synthesized compounds has also been done. </p>

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ChemInform Abstract: Multicomponent Hetero‐[4 + 2] Cycloaddition/Allylboration Reaction: From Natural Product Synthesis to Drug Discovery

Abstract: Review: 48 refs.

Cited by 2 publications

References 1 publication

Designer “Quasi-Benzyne”: The Spontaneous Reduction of Ortho-Diiodotetrafluorobenzene on Water Microdroplets

Designer “Quasi-Benzyne”: The Spontaneous Reduction of Ortho-Diiodotetrafluorobenzene on Water Microdroplets

One pot synthesis of some novel indole derivatives and their antimicrobial activity

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