C–H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(15), P. 6738 - 6756

Published: Jan. 1, 2022

Sequential multicomponent C–H bond addition is a powerful approach for the rapid, modular generation of molecular complexity in single reaction.

Language: Английский

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Iridium-Catalyzed Branch-Selective and Enantioselective Hydroalkenylation of α-Olefins through C–H Cleavage of Enamides

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(38), P. 17351 - 17358

Published: Sept. 19, 2022

Catalytic branch-selective hydrofunctionalization of feedstock α-olefins to form enantioenriched chiral compounds is a particularly attractive yet challenging transformation in asymmetric catalysis. Herein we report an iridium-catalyzed hydroalkenylation through directed C–H cleavage enamides. This atom-economical addition process highly and enantioselective, delivering trisubstituted alkenes with allylic stereocenter. DFT calculations reveal the origin regio- enantioselectivity.

Language: Английский

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Cobalt-Catalyzed Three-Component Assembling of Aromatic Oximes with Substituted Dienes and Formaldehyde

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10540 - 10543

Published: Jan. 1, 2024

A cobalt-catalyzed three-component assembly of substituted aryl oximes with dienes and formaldehyde

Language: Английский

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Co(III)-Catalyzed Three-Component Assembling of 2-Pyridones with Dienes and Formaldehyde via C–H Bond Activation

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Here, we have demonstrated a Co(III)-catalyzed C–H functionalization of substituted pyridones with dienes and para-formaldehyde via three-component sequential reaction. A library homoallylic alcohols is synthesized high regio- chemoselectivity. The reaction scope widely compatible various N-pyridyl-2-pyridones, butadiene, dienes. Interestingly, N-pyridyl-4-pyridone also participated in the product was further converted into dihydrofuran-derived N-pyridyl-2-pyridone derivatives. convincing mechanism mechanistic investigations are described to justify current methodology.

Language: Английский

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A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes

Chemical Science, Journal Year: 2023, Volume and Issue: 14(28), P. 7709 - 7715

Published: Jan. 1, 2023

A novel three-component protocol to synthesize trisubstituted allenes from 2-alkynyl-1,4-diol dicarbonate with organoboronic acid and malonate has been developed.

Language: Английский

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Palladium‐Catalyzed Ring‐Closing Aminoalkylative Amination of Unactivated Aminoenynes

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(3)

Published: Nov. 21, 2022

An efficient strategy for preventing the β-hydride elimination of alkylpalladium species by ligation palladium with adjacent amino-group was developed, which enabled a novel palladium-catalyzed ring-closing aminoalkylative amination unactivated aminoenynes. The reaction is amenable to aminals, as well aliphatic aldehydes secondary amines, provides straightforward access structurally diverse exocyclic allenic amines bearing 5 12-membered N-heterocycles. With chiral phosphoramidite-ligated complex catalyst, an enantioselective variant achieved up 93 % ee. Simultaneously, synthetic transformations products were also conducted afford unique spirodiamines including one pharmaceutically active molecule via axial-to-central chirality transfer.

Language: Английский

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Cascade Multicomponent Assemblies Involving 1,3-Enynes via Auto-Tandem Palladium Catalysis

Organic Letters, Journal Year: 2022, Volume and Issue: 24(34), P. 6326 - 6330

Published: Aug. 23, 2022

Here we report a three-component auto-tandem reaction of 1,3-enyne-tethered carbonyls, organoboronic reagents, and suitable nucleophiles catalyzed by palladium, proceeding through consecutive intramolecular vinylogous addition, Suzuki coupling, allylic alkylation. This process exhibited high chemo- regioselectivity with 1,3,4-trifunctionalization the 1,3-enyne motif, wide range 2H-chromenes, 1,2-dihydroquinolines, benzo[b]oxepines, 1,7-annulated indoles, other frameworks were efficiently constructed in fair to good yields E/Z selectivity.

Language: Английский

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Three-component regioselective carboamidation of 1,3-enynes via rhodium(iii)-catalyzed C–H activation

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(44), P. 6690 - 6693

Published: Jan. 1, 2023

Rhodium-catalyzed regio- and stereoselective three-component carboamidation of 1,3-enynes has been realized using indoles dioxazolones as the functionalizing reagents. A wide range multi-substituted skipped 1,4-dienes have constructed in good yields excellent stereoselectivity. The stereoselectivity is under substrate control. 1,3-Enynes bearing a relatively bulky alkyne terminus reacted with Z-selectivity. In contrast, sterically less hindered tends to predominantly give E-configured diene.

Language: Английский

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Synthesis of Diverse Allylic Sulfone Derivatives via Sequential Hydroalkoxylation of 1,3‐Enynes

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(42)

Published: May 7, 2024

Abstract A first metal‐free protocol for the synthesis of allylic sulfones featuring aldehyde functionality at δ‐position has been reported. The formation structurally complex δ,δ‐dimethoxy is enabled by direct nucleophilic attack methoxide onto sulfone‐containing 1,3‐enynes. present approach allows facile installation acetal groups within sulfone scaffold, providing versatile platforms further functionalization and drug development.

Language: Английский

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Chemo- and regioselective cyclization of diene-tethered enynesviapalladium-catalyzed aminomethylamination

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 2988 - 2993

Published: Jan. 1, 2023

A chemo- and regioselective cyclization of diene-tethered enynes via palladium-catalyzed aminomethylamination is established for the synthesis functionalized benzofulvenes.

Language: Английский

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