Boryl Radical as a Catalyst in Enabling Intra‐ and Intermolecular Cascade Radical Cyclization Reactions: Construction of Polycyclic Molecules DOI
Jie Wang, Yee Lin Phang,

You‐Jie Yu

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(25)

Опубликована: Апрель 9, 2024

Abstract Cascade radical cyclization constitutes an atom‐ and step‐economic route for rapid assembly of polycyclic molecular skeletons. Although array redox‐active metal catalysts has recently shown robust applications in enabling various catalytic cascade processes, the use free organic as catalyst, which is capable triggering strategically distinct cascades, rarely been developed. Here, we disclosed that benzimidazolium‐based N ‐heterocyclic carbene (NHC)‐boryl catalyzing reactions both intra‐ intermolecular pathways, assembling [5,5] fused bicyclic [6,6,6] tricyclic molecules, respectively. The start with chemo‐ regioselective addition boryl catalyst to a tethered alkene or alkyne moiety, followed by either intramolecular formal [3+2] [2+2+2] cycloaddition process construct bicyclo[3.3.0]octane tetrahydrophenanthridine skeletons, Eventually, β‐elimination occurs release completing cycle. High excellent diastereoselectivity achieved under substrate control.

Язык: Английский

Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle DOI Creative Commons
Huimin Jiang, Yilin Zhao, Qing Sun

и другие.

Molecules, Год журнала: 2023, Номер 28(4), С. 1775 - 1775

Опубликована: Фев. 13, 2023

Oximes and hydroxylamines are a very important class of skeletons that not only widely exist in natural products drug molecules, but also synthon, which have been used industrial production. Due to weak N-O σ bonds oximes hydroxylamines, they can be easily transformed into other functional groups by bond cleavage. Therefore, the synthesis N-heterocycle using as nitrogen sources has attracted wide attention. Recent advances for through transition-metal-catalyzed radical-mediated cyclization classified type rings summarized. In this paper, recent cleavage reviewed. We hope review provides new perspective on field, reference develop environmentally friendly sustainable methods.

Язык: Английский

Процитировано

16

Navigating Visible‐Light‐Triggered (aza and thia) Paternò‐Büchi Reactions for the Synthesis of Heterocycles DOI Open Access
Qing‐Bao Zhang, Yongqi Yang, Shanshan Zhang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(21), С. 3556 - 3571

Опубликована: Авг. 2, 2023

Abstract Harnessing visible light to trigger (aza and thia) Paternò‐Büchi reaction injects new vitality into [2+2] photocyclization enable impressive reactivity modes. The popular is one of the most efficient ways synthesize strained four‐membered heterocycles. Recently, visible‐light‐triggered reactions have received considerable attentions as this strategy has overcome some long‐standing challenges, remarkable achievements been made within field. Strained heterocyclics with favorable properties provide a perfect combination stable skeletons for pharmaceutical chemistry intermediates further transformation. In review, we highlight recent advances in an emphasis on mechanism applications. Organization review follows subdivision according type substrate classes.

Язык: Английский

Процитировано

15

Molecular Design and Biomedical Application of AIEgens with Photochemical Activity DOI Creative Commons
Jianqing Li,

Zeyan Zhuang,

Xiaoding Lou

и другие.

Chemical & Biomedical Imaging, Год журнала: 2023, Номер 1(9), С. 785 - 795

Опубликована: Май 19, 2023

Photochemical reaction is expected to become a promising type of green chemistry with merits operational flexibility, excellent regioselectivity, high yield, and mild condition. Recently, aggregation-induced emission (AIE)-based fluorescent molecules photoresponsivity have been quickly developed employed in the biomedical field. In this Review, photoresponsive AIE materials based on inherent photochemical reactions are highlighted according pathways: photoisomerization, photocyclization, photodimerization, multiple photoreactions. Following this, their applications summarized discussed, including photoactivatable bioimaging, diagnosis, therapy. Finally, challenges future perspectives presented.

Язык: Английский

Процитировано

14

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst DOI Creative Commons

Bohang An,

Hao Cui, Chao Zheng

и другие.

Chemical Science, Год журнала: 2024, Номер 15(11), С. 4114 - 4120

Опубликована: Янв. 1, 2024

Starting from the same substrates, tunable C–H functionalization and dearomatization have been achieved under catalysis of a new organic photocatalyst – isoazatruxene ITN-2.

Язык: Английский

Процитировано

5

Boryl Radical as a Catalyst in Enabling Intra‐ and Intermolecular Cascade Radical Cyclization Reactions: Construction of Polycyclic Molecules DOI
Jie Wang, Yee Lin Phang,

You‐Jie Yu

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(25)

Опубликована: Апрель 9, 2024

Abstract Cascade radical cyclization constitutes an atom‐ and step‐economic route for rapid assembly of polycyclic molecular skeletons. Although array redox‐active metal catalysts has recently shown robust applications in enabling various catalytic cascade processes, the use free organic as catalyst, which is capable triggering strategically distinct cascades, rarely been developed. Here, we disclosed that benzimidazolium‐based N ‐heterocyclic carbene (NHC)‐boryl catalyzing reactions both intra‐ intermolecular pathways, assembling [5,5] fused bicyclic [6,6,6] tricyclic molecules, respectively. The start with chemo‐ regioselective addition boryl catalyst to a tethered alkene or alkyne moiety, followed by either intramolecular formal [3+2] [2+2+2] cycloaddition process construct bicyclo[3.3.0]octane tetrahydrophenanthridine skeletons, Eventually, β‐elimination occurs release completing cycle. High excellent diastereoselectivity achieved under substrate control.

Язык: Английский

Процитировано

5