Homogeneous Gold Catalysis for Regioselective Carbocyclization of Alkynyl Precursors

ChemPlusChem, Journal Year: 2023, Volume and Issue: 88(7)

Published: June 7, 2023

Abstract π‐Activation of alkynyl precursors possessing an endogenous carbon nucleophile is one the imperative topics in homogeneous gold catalysis as it offers Csp 3 ‐Csp 2 and linked carbocycles. However, exo ‐ dig endo cyclization modes unlocks possibility both small large rings respectively, thereby losing regioselectivity. Nevertheless, several gold‐catalyzed carbocyclizations which permits isomer by controlling or avoiding formation other went largely unnoticed. Hence, this review attempt to summarize such approaches reported from early 2000’s till date along with our viewpoint on contributing parameters for This covers only unimolecular reactions classifications primarily based type nucleophiles silyloxyenols, enamides/enamines, benzenoids, heteroaromatics alkyls/alkenyls. From application perspective, these are significant total synthesis materials science. Therefore, those that finds natural product π‐functional highlighted appropriate places.

Language: Английский

---

Gold-Catalyzed Cascade Cycloisomerization of 3-Allyloxy-1,6-diynes to Cyclopropyl- and Cyclobutyl-Fused Benzofurans and Chromen-3a(1H)-ols

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2635 - 2640

Published: March 25, 2024

A synthetic method for the efficient preparation of partially hydrogenated benzo[f]cyclobuta[cd]cyclopenta[h]benzofurans and cyclopropa[c]chromen-3a(1H)-ols that relies on gold(I)-catalyzed cascade cycloisomerization 3-allyloxy-1,6-diynes is described.

Language: Английский

---

Brønsted Acid-Catalyzed Intramolecular Tandem Double Cyclization of γ-Hydroxy Acetylenic Ketones with Alkynes into Naphtho[1,2-b]furan-3-ones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1633 - 1647

Published: Jan. 18, 2024

A metal-free and atom-economic route for the synthesis of naphtho[1,2-b]furan-3-ones has been realized via p-TsOH·H2O-catalyzed intramolecular tandem double cyclization γ-hydroxy acetylenic ketones with alkynes in formic acid. The benzene-linked furanonyl-ynes are key intermediates obtained by scission/recombination C–O bonds. Further, structural modifications representative product were implemented reduction, demethylation, substitution, [5 + 2]-cycloaddition.

Language: Английский

---

Gold-catalyzed synthesis of small-sized carbo- and heterocyclic compounds: A review

Heterocyclic Communications, Journal Year: 2024, Volume and Issue: 30(1)

Published: Jan. 1, 2024

Abstract Research on gold catalysis has flourished over the last 20 years, and catalysts are now acknowledged as “best choice” for a range of organic transformations. Gold complexes have emerged promising candidates this use in recent years because their high reactivity, which enables them to induce broad transformations under mild conditions. Extensive demonstrations showcased extraordinary efficiency synthesizing complex compounds from basic starting components. In addition its traditional applications catalysis, expanded include total synthesis natural compounds, is demanding undertaking. The class molecules known carbo- heterocycles, arguably most important, significant impact agrochemicals pharmaceuticals among numerous additional products made possible by novel procedures pioneered. main topic review how Au salts homogeneous create cyclization processes small heterocyclic carbocyclic systems. This study gives an overview books articles written after 2013 that discuss making three- four-membered rings with catalyst. We every effort all outstanding reports subject; nonetheless, we apologize any omissions.

Language: Английский

---

Gold(I)‐Catalyzed Regioselective Synthesis of Indenylidene Derivatives via 1,5‐Acryl Migration

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(14)

Published: May 8, 2024

A novel gold (I)-catalyzed synthetic strategy has been achieved for an efficient construction of indenylidene derivatives from substituted 1,6-diynes. This reaction describes the unique reactivity catalysis in facilitating intramolecular [3,3]-sigmatropic rearrangement, 5-exo dig cyclization followed by 1,5-migration acryl group, resulting formation indenylidenes. Various indenylidenes were successfully synthesized with up to 92 % yields. In this protocol, two new C-C bonds sequentially formed atom economically one pot.

Language: Английский

---

Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization

Tetrahedron, Journal Year: 2024, Volume and Issue: 168, P. 134340 - 134340

Published: Nov. 2, 2024

Language: Английский

---

Synthesis of Isoquinoline-Derived Diene Esters and Quinolin-2(1H)-ylidene-Substituted 1,5-Diones from Enynones and (Iso) Quinoline N-Oxides

Organic Letters, Journal Year: 2022, Volume and Issue: 25(1), P. 115 - 119

Published: Dec. 30, 2022

An efficient synthetic method was developed to access isoquinoline-derived diene esters from enynones and isoquinoline-N-oxides in an atom-economic manner. The isoquinoline-substituted were obtained moderate excellent yields via [3 + 2]-cycloaddition isoxazole ring opening followed by a [1,5]-sigmatropic rearrangement reaction, which resulted one C–C two C–O bond formations. Further, quinolin-2(1H)-ylidene-substituted 1,5-diones achieved reaction of with quinoline-N-oxides very good high yields.

Language: Английский

---

Dual gold-catalyzed regioselective synthesis of benzofulvenes via 5-endo dig cyclization

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(38), P. 7799 - 7807

Published: Jan. 1, 2023

Gold-catalyzed regioselective synthesis of benzofulvenes has been developed from substituted allyloxy 1,5-diynes via 5- endo dig cyclization.

Language: Английский

---

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

Molecules, Journal Year: 2022, Volume and Issue: 27(24), P. 8956 - 8956

Published: Dec. 15, 2022

Gold catalysts possess the advantages of water and oxygen resistance, with possibility catalyzing many novel chemical transformations, especially in syntheses small-molecule skeletons, addition to achieving rapid construction multiple bonds ring systems one step. In this feature paper, we summarize recent advances scaffolds, such as benzene, cyclopentene, furan, pyran, based on gold-catalyzed cyclization arylalkyne derivatives within last decade. We hope that review will serve a useful reference for chemists apply strategies related natural products active molecules, hopefully providing guidance exploration additional approaches.

Language: Английский

---

Silver‐catalyzed Regioselective Synthesis of N‐aryl‐1H‐pyrazolyl‐substituted Benzenesulfonamides from Ynamides and Pyrazoles

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(15)

Published: June 21, 2023

Silver-catalyzed N-aryl-1H-pyrazolyl substituted benzenesulfonamide derivatives were obtained regioselectively from ynamides and pyrazoles. In this intermolecular organic transformation, several benzenesulfonamides in good to excellent yields by forming a new C-N bond under mild reaction conditions.

Language: Английский

---