Recent Progress in Arylmetalative Cyclization/Annulation of Functionalized Alkynes with Organoboranes DOI
Manda Rajesh,

Gadi Ranjith Kumar

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 19, 2023

Abstract Achieving complex molecular assemblies in modular modes is always one of the top priorities organic chemist. Cyclization/annulation functionalized alkynes through carbo metalation has an impactful swath synthetic chemistry. There have recently been considerable contributions this arena uncovering several new chemical spaces towards solutions for various fields biology. On other hand, organoboronic reagents are fascinating reactive chemprobs, partake a broad range transformations. Particularly utility these carbo‐metalation subject high perusal To degree, tuning transition‐metal catalysts with organoboranes and intriguing synthesis classes acyclic cyclic adducts. Mechanistically, arylative cyclizations proceed initial aryl‐metalation on which provides alkenyl metal species, that concomitantly react pendent electrophile. The stereo‐ regioselective reactivity C‐metal steered by chelation coordinating group and/or electrophile alkyne. In review, we focused critical achievements field emphasis stereoselective capture vinyl field, compilation detailed mechanistic pathways realm would be helpful to find gaps hence discover novel

Язык: Английский

P,N Ligand in Ni-Catalyzed Cross-Coupling Reactions: A Promising Tool for π-Functionalization DOI
Jae‐Han Bae, Eun Jin Cho

ACS Catalysis, Год журнала: 2023, Номер 13(20), С. 13540 - 13560

Опубликована: Окт. 6, 2023

Bidentate P,N ligands, integrating phosphine and nitrogen donors, are highlighted for their versatile characteristics, offering both electronic steric tunability. Their hemilabile nature, coupled with the ability to modulate properties through choice of donor atoms substituents, has expanded horizons chemical transformations. This Review focuses on Ni-catalyzed cross-coupling reactions mediated by ligands. The asymmetrical nature each atom playing a specific role in catalytic cycle, offers control, stability, unique regioselectivity processes. In particular, Ni/P,N-catalytic system exhibits remarkable reactivity π-substrates including alkenes, alkynes, allenes. A thorough mechanistic understanding these processes insights into trends future directions Ni/P,N-catalyzed reactions.

Язык: Английский

Процитировано

15

Enantioselective Nickel‐Catalyzed anti‐Arylmetallative Cyclizations onto Acyclic Ketones DOI Creative Commons

Harley Green,

Stephen P. Argent, Hon Wai Lam

и другие.

Chemistry - A European Journal, Год журнала: 2021, Номер 27(19), С. 5897 - 5900

Опубликована: Фев. 5, 2021

Abstract Domino reactions involving nickel‐catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization the alkenylnickel intermediates onto tethered acyclic ketones give chiral tertiary‐alcohol‐containing products in high enantioselectivities, are described. The reversible E / Z isomerization enables overall anti ‐arylmetallative occur. ring system substructures certain diarylindolizidine alkaloids.

Язык: Английский

Процитировано

28

Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress DOI

Divyang M. Patel,

Paras J. Patel,

Hitendra M. Patel

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(46)

Опубликована: Ноя. 16, 2022

Abstract Spiro derivatives are important scaffolding substances found in many natural products and pharmaceuticals. In the last decade, numerous new approaches based on multicomponent reactions have been explored for selective efficient development of spiro using various organocatalytic transition metal‐based catalytic systems. This Review discusses pioneering advances field stereoselective preparation derivatives. These include Michael cascade cyclization reactions, cycloadditions, diastereoselective miscellaneous synthesis spiro‐hetero/carbocycles. Advances decade made it possible to synthesize compounds with good excellent stereoselectivity under appropriate reaction conditions. However, achieving high regioselectivity several described remains a challenge. Organocatalysts transition‐metal‐based catalysts play crucial role this milestone. Proposed mechanisms supporting evidence highlighted Review. The progress is immense. expected that synthetic methods will soon be developed can widely used spiro‐heterocycles/carbocycles.

Язык: Английский

Процитировано

20

Atroposelective Synthesis of C−N Vinylindole Atropisomers by Palladium‐Catalyzed Asymmetric Hydroarylation of 1‐Alkynylindoles DOI

Li‐Wen Zhan,

Chuan‐Jun Lu, Jia Feng

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(45)

Опубликована: Сен. 25, 2023

Transition-metal-catalyzed hydroarylation of unsymmetrical internal alkynes remains challenging because the difficulty in controlling regioselectivity and stereoselectivity. Moreover, enantioselective using organoboron reagents has not been reported. Herein, we report for first time that palladium compounds can catalyze 1-alkynylindoles with organoborons synthesis chiral C-N atropisomers. A series rarely reported vinylindole atropisomers was synthesized excellent regio-, stereo- (Z-selectivity), enantioselectivity under mild reaction conditions. The ready availability simplicity, high stereoselectivity, good functional group tolerance this catalytic system make it highly attractive.

Язык: Английский

Процитировано

12

Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions DOI Open Access
Yanyan Zhang,

Zhuzhu Zhang,

Shengqing Zhu

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(3), С. 1023 - 1023

Опубликована: Янв. 1, 2023

Chiral α-carbonyl compounds are important structural units in natural products and pharmaceuticals versatile synthetic building blocks organic synthesis.Transition metal-catalyzed asymmetric acylation reaction is one of the most straightforward methods for preparing these compounds.In particular, significant progress has been made area nickel-catalyzed reaction, due to unique properties nickel catalysts.The latest including alkyl-acyl cross-coupling hydroacylation alkene acyl-functionalization alkene, summarized.

Язык: Английский

Процитировано

10

Recent Advances in Nonprecious Metal Catalysis DOI
Robert A. Singer, Sébastien Monfette, David J. Bernhardson

и другие.

Organic Process Research & Development, Год журнала: 2020, Номер 24(6), С. 909 - 915

Опубликована: Май 14, 2020

Nonprecious metal catalysis is a highly active area of research for both industrial and academic laboratories. New methods that efficiently generate useful functionality in cost-effective, high yielding, environmentally friendly ways naturally garner attention from process chemists many different industries. This series highlights summarizes literature on the general topic nonprecious over four-month timeframes will focus major trends field are interest pharmaceutical industry. The first installment selected transformations using copper, nickel, iron catalysts.

Язык: Английский

Процитировано

25

Asymmetric Vicinal and Remote Hydroamination of Olefins by Employing a Heck-Reaction-Derived Hydride Source DOI

Ruijie Mi,

Xuejing Yao, Youzhi Xu

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Май 6, 2025

Metal hydrides are reactive intermediates in numerous catalytic processes. In many processes, metal formed, but their potential reactivity is often wasted by reaction with a base or an oxidant to permit catalyst turnover. this report, the hydroamination of unactivated olefins described coupling Heck between aryl boronic acid, olefin, and nitrene precursor dioxazolone. Initiated olefin arylboroic rhodium hydride intermediate generated retained for second equivalent olefin. Depending on chain length alkyl group α- β-amino amides were obtained excellent regio- enantioselectivity via direct remote (migratory) hydroamination, respectively. The system features broad scope, mild conditions, enantioselectivity, it also represents rare example asymmetric using chiral rhodium(III) cyclopentadienyl catalyst. Mechanistic studies delineated turnover-limiting enantio-determining steps system.

Язык: Английский

Процитировано

0

Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions DOI

Guanxin Zhu,

Zheng‐Chao Duan, Haiyan Zhu

и другие.

Molecular Catalysis, Год журнала: 2021, Номер 505, С. 111516 - 111516

Опубликована: Март 23, 2021

Язык: Английский

Процитировано

19

Recent developments in nickel-catalyzed asymmetric cyclization and cycloaddition of carbonyl-alkynes, cyano-alkynes, and enynes DOI

Jun Yan,

Min Shi, Yin Wei

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(30), С. 4405 - 4422

Опубликована: Янв. 1, 2023

Alkynes as unsaturated hydrocarbons have long been used for cyclization reactions. Various transition metal-catalyzed cyclizations of alkynes reported in the past decades. In this minireview, we mainly summarize recent asymmetric with other functional groups such carbonyl-alkynes, cyano-alkynes, and enynes under catalytic system nickel chiral ligands.

Язык: Английский

Процитировано

8

Synergistic Pd/Cu-catalyzed regio- and stereoselective cascade Heck cyclization/borylation/cross-coupling DOI

Yifan Wang,

Yuanyuan Ping, Wangqing Kong

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 34(12), С. 108453 - 108453

Опубликована: Апрель 14, 2023

Язык: Английский

Процитировано

8