NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation DOI Open Access
Yousuke Yamaoka, Hideto Miyabe

Catalysts, Год журнала: 2024, Номер 14(4), С. 219 - 219

Опубликована: Март 22, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) have opened new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C–O bond formation based on activation aldehyde C(sp2)–H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst also described.

Язык: Английский

Enhanced Efficiency of Amide‐Substituted Quinuclidine‐Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins DOI
Yang Xiao,

Mengsi Ma,

Meichen Xu

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary An amide‐substituted quinuclidine‐borane has been identified as a more efficient hydridic hydrogen atom transfer (HAT) catalyst for the hydroalkylation of unactivated olefins under visible‐light irradiation. 1 H NMR titration experiments reveal that amide moiety forms stronger bonds with carbonyl substrates, thereby improving reaction yields. Furthermore, it was found yields correlate well association constant between and substrate. A scale‐up using continuous‐flow photoreactor also demonstrated.

Язык: Английский

Процитировано

2

Catalytic Asymmetric Oxidative Coupling between C(sp3)–H Bonds and Carboxylic Acids DOI
Xianming Liu, Fu Li,

Tongkun Wang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 17, 2024

The direct enantioselective functionalization of C(sp3)–H bonds in organic molecules could fundamentally transform the synthesis chiral molecules. In particular, oxidation these would dramatically change production methods alcohols and esters, which are prevalent natural products, pharmaceuticals, fine chemicals. Remarkable advances have been made construction carbon–carbon carbon–nitrogen through bond functionalization. However, formation carbon–oxygen from remains a considerable challenge. We herein report highly oxidative coupling with carboxylic acids. method applies to allylic propargylic C–H employs various acids as oxygenating agents. successfully synthesized range esters directly readily available alkenes alkynes, greatly simplifying related alcohols.

Язык: Английский

Процитировано

2

Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons DOI
Karthick Govindan, Alageswaran Jayaram,

Vijay Thavasianandam Seenivasan

и другие.

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Май 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Язык: Английский

Процитировано

2

NHC-Catalyzed Cross-Coupling of Aldehydes for C(sp2)−O Bond Formation DOI Open Access
Yousuke Yamaoka, Hideto Miyabe

Опубликована: Март 7, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) open new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C−O bond formation based on activation aldehyde C(sp2)−H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst is also described.

Язык: Английский

Процитировано

1

NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation DOI Open Access
Yousuke Yamaoka, Hideto Miyabe

Catalysts, Год журнала: 2024, Номер 14(4), С. 219 - 219

Опубликована: Март 22, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) have opened new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C–O bond formation based on activation aldehyde C(sp2)–H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst also described.

Язык: Английский

Процитировано

1