European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 28, 2024
Abstract An efficient method has been developed for the preparation of 1,4‐naphthoquinones via a palladium‐catalyzed reaction 2‐aryl‐1,3‐indandiones with olefins. This involves tertiary C−H alkylation olefins to produce alcohol, followed by C−C bond cleavage.
Language: Английский
ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(4), P. 2234 - 2239
Published: Jan. 27, 2023
The palladium-catalyzed skeletal rearrangement of 3-arylcyclobutanones into 1-indanones is reported. A Pd(0)/IMes catalyst allows for the cleavage C(carbonyl)–C(sp3) and C(sp2)–H bonds to result in rearrangement, neither an extra reactive functional group nor a directing required promote reaction. Deuterium-labeling experiments indicate that C–C bond initially activated subsequent C–H activation involved rate-determining step.
Language: Английский
Citations
18
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2662 - 2669
Published: Jan. 1, 2024
The mechanism of organocatalytic C-C bond activation have been theoretically investigated.
Language: Английский
Citations
9
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: March 24, 2025
We have developed a palladium-catalyzed ester carbonylation reaction that enables the synthesis of ester-substituted benzofuran derivatives in single step through introduction alkyl halides undergoing situ hydrolysis and alkynyl aryl iodides. This method demonstrates broad applicability to both primary secondary while maintaining excellent functional group compatibility under low palladium loading conditions. Notably, this strategy significantly expands scope reactions.
Language: Английский
Citations
1
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7741 - 7746
Published: May 14, 2024
A novel three-component cyclization carbonylation reaction of iodoarene-tethered propargyl ethers with amine and CO is reported. This palladium-catalyzed cascade undergoes a sequence oxidative addition, unsaturated bond migration, carbonyl insertion, nucleophilic attack to deliver the benzofuran skeleton. Both aromatic amines aliphatic could proceed smoothly in this transformation under one atm CO.
Language: Английский
Citations
6
Chemical Communications, Journal Year: 2023, Volume and Issue: 59(23), P. 3373 - 3382
Published: Jan. 1, 2023
This article summarizes recent efforts in developing enantioselective palladium- and nickel-catalyzed ring-opening/coupling reactions of cyclobutanones with a tethered aryl halide.
Language: Английский
Citations
12
Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2306 - 2311
Published: March 29, 2023
A novel and efficient method for the catalytic installation of a carbonyl group via remote radical coupling is disclosed. The nickel-catalyzed reaction proceeds to undergo sequential single-electron transfer, 1,5-hydrogen atom insertion, thus providing α-substituted ketone. Further, this could be carried out smoothly under normal pressure redox-neutral conditions, demonstrated functional-group compatibility excellent site-selectivity.
Language: Английский
Citations
9
Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 2913 - 2917
Published: April 3, 2024
C–C σ-bond cleavage and reconstruction is a significant tool for structural modification in synthetic chemistry but it remains formidable challenge to perform on unstrained skeletons. Herein, we describe radical addition-enabled cleavage/reconstruction reaction of allyl ketones access various functional indanones bearing benzylic quaternary center. The utility this method has been showcased by the first total synthesis carexane L, an indanone-based natural product.
Language: Английский
Citations
3
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: July 2, 2024
Abstract A Pd‐catalyzed carbonylative Heck reaction of 2‐iodophenyl alkenyl ether using Mo(CO) 6 as a safe CO source has been developed. This research provides an atom‐economic and straightforward route for the efficient construction benzofuran‐3(2 H )‐one scaffolds with C2 quaternary center in moderate to good yields, which features operational safety, functional group compatibility easy scale‐up.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: April 9, 2025
Palladium-catalyzed asymmetric transformations involving cyanide anions remain a challenge due to the strong affinity between and palladium, which induces alterations in coordination sphere of palladium center. Herein, palladium-catalyzed enantioselective cyanation is achieved via ring-opening/cross-coupling process aryl halide-tethered cyclobutanones Zn(CN)2. This reaction demonstrated exhibit broad substrate scope robust enantioselectivity. The synthetic utility highlighted by converting product into amide, carboxylic acid, ester without racemization.
Language: Английский
Citations
0
Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 17, 2025
Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.
Language: Английский
Citations
0