Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(16), P. 3355 - 3359
Published: Jan. 1, 2023
A simple and novel Pd-catalysed cross-coupling reaction of allenylic carbonates with different gem-diborylalkanes was developed. Under mild conditions, synthetically useful versatile isoprenylboronates could be obtained selectively in moderate to high yields. Furthermore, the utility isoprenylboronate is demonstrated through isoprenylboration homologation.
Language: Английский
Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(37), P. 15654 - 15660
Published: Aug. 26, 2020
Herein, we report a nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide to access the chiral α-alkylated pyrrolidinone broad substrate scope and high enantiomeric excess. The current art synthesis still remains challenging on enantioselective α-monoalkylation pyrrolidinones. newly designed 8-quinoline imidazoline ligand (Quinim) is crucial for maintaining reactivity enantioselectivity ensure cyclization monosubstituted alkenes unprecedented non-aromatic heterocycles.
Language: Английский
Citations
109
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(36)
Published: July 12, 2022
Herein, we leverage the Ni-catalyzed enantioselective reductive dicarbofunctionalization of internal alkenes with alkyl iodides to enable synthesis chiral pyrrolidinones bearing vicinal stereogenic centers. The application newly developed
Language: Английский
Citations
30
Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(14), P. 1673 - 1678
Published: Feb. 14, 2023
Comprehensive Summary Transition metal‐catalyzed difunctionalization of tethered alkene has emerged as a prevailing tool for the expedient construction synthetically valuable cyclic compounds. However, most efforts have been devoted to reaction styrene‐type substrates due their rigid scaffold and high reactivity. With respect nonaromatic olefin, especially mono‐substituted alkene, still remains largely underdeveloped. Herein, we disclose nickel/Quinim complex TBADT‐cocatalyzed asymmetric carbamoyl‐acylation unactivated on carbamoyl chlorides with diverse aldehydes. The exhibits broad substrate scope good functional group tolerance, well efficiency enantioselectivity. Both monosubstituted 1,1‐substituted alkenes can work either aliphatic or aromatic aldehydes under current protocol, providing convenient access an array medicinally useful chiral γ‐lactams derivatives bearing convertible acyl functionality. This showcases more application possibilities Quinim ligand in future catalytic transformations.
Language: Английский
Citations
19
The Chemical Record, Journal Year: 2024, Volume and Issue: 24(3)
Published: Feb. 2, 2024
Abstract The wide applications of alpha‐boryl carbanions in selective coupling with organohalides, imines/carbonyls and conjugated unsaturated substrates has become an interesting tool for organic synthesis. Strategically, the inclusion heteroatoms, such as Si, S, N, F, Cl, Br I alpha position opens a new venue towards multifunctionalities molecular design. Here, conceptual practical view on powerful carbanions, containing α‐silicoboron, α‐thioboron, α‐haloboron α‐aminoboron is given, well prespective their efficient application electrophilic trapping.
Language: Английский
Citations
7
Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(14), P. 4024 - 4045
Published: Jan. 1, 2021
This review highlights the recent advancements of carbamoyl chlorides in transition metal-catalyzed reactions to access various amide-containing molecules and heterocycles.
Language: Английский
Citations
34
Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(9), P. 2274 - 2289
Published: March 10, 2021
Abstract α‐Monoboryl anions show remarkable stability due to the valence deficiency of adjacent three‐coordinate boron center and can be expressed as its resonance form, borata‐alkene systems [R 2 B=CH ] − . The diversity synthetic approaches well properties C=B bond are disclosed in this review, dealing with both electronic structural boryl moieties involved. Full characterization solid state by X‐ray diffraction demonstrated short distances between B C, a consequence ylide character boron‐stabilized carbanions. This review includes collection C−B length 11 NMR data that useful for diagnostic evidence partial boron‐carbon double‐bond character. Natural orbital (NBO) analysis on DFT computed structures also supports justifies reactivity acting nucleophilic synthon is unveiled through extensive electrophilic trapping examples. homologation protocols diborylmethane, via single carbon chain extension, involves facile introduction C( sp 3 )−B bonds, which subsequently transformed into functionalized target products, containing C−O, C−N or C−C bonds. magnified image
Language: Английский
Citations
33
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(15), P. 2436 - 2466
Published: June 12, 2023
Abstract Elaborated molecular architectures including complex carbocycles, heterocycles, and polycyclic structures represent an important class of organic compounds because they are ubiquitous structural units in a broad variety biologically pharmacologically relevant natural products, medicinal molecules, functional materials. A major challenge modern synthetic methodology is the development strategically efficient selective construction these from readily available starting Transition‐metal‐catalyzed transformations involving Heck reaction as pivotal step have afforded powerful approach for accessing sophisticated skeletons set easy‐to handle materials, thus highlighting its potential significance streamlining drug discovery process. Over past few decades, significant effort has been devoted to derivatives versatile routes, number direct strategies reported. In this review, latest advances transition‐metal‐catalyzed critical summarized, which could be divided into six categories: 1) Heck/Sonogashira tandem reaction; 2) Heck/Suzuki 3) Heck/Heck 4) Heck/Hiyama 5) Heck/Cacchi 6) Heck/C−H bond functionalization reaction.
Language: Английский
Citations
16
Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2297 - 2302
Published: March 11, 2024
We report a deoxygenative amidation reaction of alcohols with carbamoyl chlorides to afford amides through nickel–photoredox dual catalysis. Good excellent yields can be obtained even for diverse complex sugar and steroid derivatives. The is scalable, the synthetic utility was demonstrated by homologation deliver several important γ-amino synthetically challenging bioactive compound intermediate.
Language: Английский
Citations
4
Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6407 - 6411
Published: Aug. 4, 2021
Herein we report a nickel-catalyzed asymmetric reductive dicarbamoylation of alkenes, in which tethered carbamoyl chlorides and isocyanates serve as distinct electrophilic carbamoylating agents, providing new access to chiral oxindoles bearing an amide-substituted quaternary stereogenic center.
Language: Английский
Citations
24
Chemical Communications, Journal Year: 2023, Volume and Issue: 59(71), P. 10620 - 10623
Published: Jan. 1, 2023
Here, a redox-neutral palladium-catalyzed photo-induced radical cascade domino Heck reaction of N-aryl acrylamide with vinyl arenes is described. A diverse range bioactive oxindoles, featuring an all-carbon quaternary center, were synthesized. The proposed to proceed via open-shell intermediate and occurs under mild conditions, exhibiting excellent functional group tolerance. Importantly, the synthesized products can be readily transformed into biologically active molecules, including (±)-physostigmine (±)-physovenine.
Language: Английский
Citations
10