European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 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.
Язык: Английский
ACS Catalysis, Год журнала: 2023, Номер 13(4), С. 2234 - 2239
Опубликована: Янв. 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.
Язык: Английский
Процитировано
18
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(13), С. 2662 - 2669
Опубликована: Янв. 1, 2024
The mechanism of organocatalytic C-C bond activation have been theoretically investigated.
Язык: Английский
Процитировано
9
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Март 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.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7741 - 7746
Опубликована: Май 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.
Язык: Английский
Процитировано
6
Chemical Communications, Год журнала: 2023, Номер 59(23), С. 3373 - 3382
Опубликована: Янв. 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.
Язык: Английский
Процитировано
12
Organic Letters, Год журнала: 2023, Номер 25(13), С. 2306 - 2311
Опубликована: Март 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.
Язык: Английский
Процитировано
9
Organic Letters, Год журнала: 2024, Номер 26(15), С. 2913 - 2917
Опубликована: Апрель 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.
Язык: Английский
Процитировано
3
European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Июль 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.
Язык: Английский
Процитировано
3
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Апрель 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.
Язык: Английский
Процитировано
0
Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Апрель 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%.
Язык: Английский
Процитировано
0