Topics in heterocyclic chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(38)
Опубликована: Июнь 7, 2023
Glycosyl radical functionalization is one of the central topics in synthetic carbohydrate chemistry. Recent advances metal-catalyzed cross-coupling chemistry and metallaphotoredox catalysis provided powerful platforms for glycosyl diversification. In particular, discovery new precursors conjunction with these advanced reaction technologies have significantly expanded space compound synthesis. this Review, we highlight most recent progress area starting from 2021, reports included will be categorized based on different types better clarity.
Язык: Английский
Процитировано
67
Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(17), С. 2217 - 2236
Опубликована: Апрель 13, 2023
Comprehensive Summary C‐Glycosides are critical, naturally occurring products and medicinal candidates, extensive efforts have been made to explore efficient approaches for creating C‐glycosidic bonds. Transition‐metal‐catalysis, particularly nickel‐catalyzed C‐glycosylation reactions constitute a promising strategy. However, achieving stereoselective synthesis of α‐ β‐C‐glycosides has long‐standing challenge. To address this problem, variety nickel‐mediated strategies developed. This review highlights recent developments in the diastereoselective briefly summarizes mechanistic understandings these methods.
Язык: Английский
Процитировано
33
ACS Catalysis, Год журнала: 2024, Номер 14(7), С. 4510 - 4522
Опубликована: Март 12, 2024
Organosilicons are privileged skeletons in the domains of pharmaceutical chemistry, organic synthesis, and materials science. Hence, investigating catalytic techniques for synthesis organosilicon compounds has received a great deal emphasis. Carbosilylation alkenes is an efficient technique to introduce diverse molecular architectures containing silicon into chemical space. However, organohalides pseudohalides prerequisites most existing carbosilylation protocols. On other hand, utilization C–H activation been sowing seeds successful development intricate scaffolds. In this regard, synthetic accessibility complexed derivatives by through meta-C–H approach remained intangible. Herein, we present three-component strategy arylsilylation olefins with (het)arenes silanes integrating iron-catalyzed silyl radical generation, coupled intrinsic reactivity alkene, ruthenium-catalyzed functionalization (het)arene, leading targeted cross-coupled carbosilylated product. addition, theoretical investigations state-of-the-art dispersion corrected density functional theory at B3PW91-D3/Def2TZVP/CPCM(PhCF3) shed intriguing insights on selectivity probable mechanistic pathway underexplored cooperative 3d/4d transition metal catalysis, such as formation its addition alkene catalyzed iron, followed meta-selective ruthenium bound arene, furnishing C4 substituted (het)arene functionalized compounds.
Язык: Английский
Процитировано
10
Organic Letters, Год журнала: 2024, Номер 26(2), С. 427 - 432
Опубликована: Янв. 8, 2024
A mild approach to the visible-light-mediated bimetal-catalyzed meta-alkylation of arenes has been accomplished. The regioselective is realized by a bimetallic ruthenium–palladium system. Ruthenium acts as catalyst for directing effect and photosensitizer, while cocatalyst palladium behaves generation fluoroalkyl radicals. This reaction not only suitable two-component meta-fluoroalkylation but can also be extended three-component reactions achieve bifunctionalization olefins.
Язык: Английский
Процитировано
8
Organic Letters, Год журнала: 2023, Номер 25(33), С. 6099 - 6104
Опубликована: Авг. 14, 2023
A visible-light-induced glycoarylation of activated olefins has been accomplished. Glycosyl radicals are generated via radical transfer strategies between (TMS)3SiOH and glycosyl bromides. Subsequent translocation rapid 1,4-aryl migration form β-sugar amide derivatives, eight types sugars compatible with this reaction. Further, the cascade reaction produced a quaternary carbon center good functional group adaptability high regioselectivity in mild conditions.
Язык: Английский
Процитировано
16
ACS Catalysis, Год журнала: 2024, Номер 14(15), С. 11532 - 11544
Опубликована: Июль 19, 2024
Glycosyl donor activation emerged as an enabling technology for anomeric functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose mechanistically distinct electrochemical glycosyl bromide activations via halogen-atom transfer and C-glycosylation. The radical addition to alkenes led C-alkyl glycoside synthesis under precious metal-free reaction conditions from readily available bromides. robustness of our e-XAT strategy was further mirrored by C-aryl C-acyl glycosides assembly through nickela-electrocatalysis. Our approach provides orthogonal with expedient scope, hence representing a general method direct C-glycosides assembly.
Язык: Английский
Процитировано
6
Angewandte Chemie, Год журнала: 2023, Номер 135(38)
Опубликована: Июнь 7, 2023
Abstract Glycosyl radical functionalization is one of the central topics in synthetic carbohydrate chemistry. Recent advances metal‐catalyzed cross‐coupling chemistry and metallaphotoredox catalysis provided powerful platforms for glycosyl diversification. In particular, discovery new precursors conjunction with these advanced reaction technologies have significantly expanded space compound synthesis. this Review, we highlight most recent progress area starting from 2021, reports included will be categorized based on different types better clarity.
Язык: Английский
Процитировано
11
Advanced Science, Год журнала: 2024, Номер 11(12)
Опубликована: Янв. 18, 2024
Among C-glycosides, C-alkyl glycosides are significant building blocks for natural products and glycopeptides. However, research on efficient construction methods remains relatively limited. Compared with Michael acceptors, non-activated olefins more challenging substrates have rarely been employed in the of C-glycosides. Here, a highly convenient approach synthesis through nickel-catalyzed C(sp
Язык: Английский
Процитировано
4
Precision Chemistry, Год журнала: 2024, Номер 2(11), С. 587 - 599
Опубликована: Июль 21, 2024
Nonclassical C-glycosides, distinguished by their unique glycosidic bond connection mode, represent a promising avenue for the development of carbohydrate-based drugs. However, accessibility nonclassical C-glycosides hinders broader investigations into structural features and modes action. Herein, we present first example Pd-catalyzed stereospecific glycosylation anomeric stannanes with aryl or vinyl halides. This method furnishes desired in good to excellent yields, while allowing exclusive control configuration. Of significant note is demonstration generality practicality this C-glycosylation approach across more than 50 examples, encompassing various protected unprotected saccharides, deoxy sugars, oligopeptides, complex molecules. Furthermore, biological evaluation indicates that modifications drug molecules can positively impact activity. Additionally, extensive computational studies are conducted elucidate rationale behind differences reaction reactivity, unveiling transmetalation transition state containing silver (Ag) within six-membered ring. Given its remarkable controllability, predictability, consistently high chemical selectivity stereospecificity regarding carbon Z/E configuration, outlined study offers solution longstanding challenge accessing stereocontrol.
Язык: Английский
Процитировано
4
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11136 - 11147
Опубликована: Авг. 6, 2024
-Alkyl glycosides, an important class of C-glycosides, are widely found in various drugs and natural products. The synthesis
Язык: Английский
Процитировано
4