Pyrrolylsulfonium salts: stable, accessible and versatile pseudohalides for Stille couplings DOI Creative Commons
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.

Язык: Английский

Composite Nanoarchitectonics Towards Method for Everything in Materials Science DOI Creative Commons
Katsuhiko Ariga

Journal of Inorganic and Organometallic Polymers and Materials, Год журнала: 2024, Номер 34(7), С. 2926 - 2947

Опубликована: Апрель 16, 2024

Abstract The characteristic feature of a biofunctional system is that components with various functions work together. These multi-components are not simply mixed together, but rationally arranged. fundamental technologies to do this in an artificial include the synthetic chemistry substances make component unit, science and techniques for assembling them, technology analyzing their nanoostructures. A new concept, nanoarchitectonics, can play role. Nanoarchitectonics post-nanotechnology concept involves building functional materials reflect nanostructures. In particular, approach combining multiple types create composite area where nanoarchitectonics be powerful tool. This review summarizes such examples related studies. presented areas catalyst & photocatalyst, energy, sensing environment, bio medical, other applications illustrate potential wide range applications. order show stages development, only state-of-the-art, also those successful developments existing research. Finally, summary brief discussion future challenges will given. applicable all aims establish ultimate methodology science.

Язык: Английский

Процитировано

5

Photoactivation of Thianthrenium Salts: An Electron-Donor–Acceptor (EDA)-Complex Approach DOI

Roshan I. Patel,

Barakha Saxena,

Anuj Sharma

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 14, 2025

Thianthrenium salts have emerged as one of the most versatile reagents, gaining significant popularity within synthetic community for their utility in construction C-C and C-X (X = N, O, S, P, halogens) bonds. The use photoredox transition metal catalysis with thianthrenium C-heteroatom bond formation is well established. However, these methods require elevated temperatures, expensive catalysts, ligands under stringent conditions effective execution. In contrast, photocatalysis- transition-metal-free approaches constructing bonds using salt derivatives become increasingly sought after. this regard, electron-donor-acceptor (EDA)-complex reactions a powerful strategy organic synthesis, eliminating need photocatalysts visible light irradiation. EDA-complex photochemistry exploits electron-acceptor properties salts, facilitating rapid generation radical intermediates via C-S cleavage. These play pivotal role enabling variety valuable formations. Perspective, we highlight advances EDA-complex-mediated involving mechanisms, substrate scope, limitations For sake brevity, article organized into five main sections: (1) Nitrogen-based donor reactions, (2) Oxygen-based (3) Sulfur-based (4) Phosphorus-based (5) π-based focus on C-C, C-S, C-B C-P

Язык: Английский

Процитировано

0

Thianthrenium-Enabled Chromium-Catalyzed Deuterated Alkyl Addition to Aldehydes via a Photoactive Electron Donor–Acceptor Complex DOI

Wenjuan Xiao,

Youye Tian,

Liting Du

и другие.

Organic Letters, Год журнала: 2025, Номер 27(5), С. 1112 - 1117

Опубликована: Янв. 23, 2025

The Nozaki-Hiyama-Kishi reaction offers effective and reliable strategies for the preparation of alcohols via carbon-carbon bond formation. Typical methods usually require stoichiometric amounts chromium salts, co-transition metals, auxiliary reagents, which limits their practical application in industrial chemistry. To mitigate these limitations, substantial efforts have been made to develop chromium-catalytic approaches. However, an excess metal reductants or expensive photocatalysts played essential roles during catalytic cycles. Here, we present a photoactive electron donor-acceptor (EDA) complex-induced chromium-catalyzed route, accomplishing alkyl addition aldehydes without requirement photocatalysts. Furthermore, on basis pH-dependent site-selective hydrogen isotope exchange thianthrenium range β-deuterated secondary could be prepared with high efficiency excellent deuterium incorporation. Mechanistic studies revealed that photoinduced intramolecular single-electron transfer EDA complex happened provide radicals are captured by Cr(II) species facilitate subsequent Meanwhile, excited Hantzsch ester act as terminal reductant turnover catalyst.

Язык: Английский

Процитировано

0

Radical Cascade Cyclization of N-(o-Cyanobiaryl)acrylamides with Sulfonium Salts via Synergetic Photoredox and Copper Catalysis DOI

Xin‐Qian Liu,

Hui Chen, Jian‐Hong Fan

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7650 - 7655

Опубликована: Сен. 4, 2024

As the magic methyl effect is well acknowledged in pharmaceutical molecules, development of simple and efficient methods for installment groups on complex molecules highly coveted. Hence, we provide a general strategy radical cascade cyclization

Язык: Английский

Процитировано

1

Thianthrenium-Enabled Chromium-Catalyzed Deuterated Alkyl Addition to Aldehydes via Photoactive Electron Donor-Acceptor Complex DOI
Binlin Zhao,

Wenjuan Xiao,

Youye Tian

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Сен. 23, 2024

Abstract The Nozaki-Hiyama-Kishi (NHK) reaction offers effective and reliable strategies for the preparation of alcohols via carbon-carbon bond formation. Typical methods usually require stoichiometric amount chromium salts, co-transition metals auxiliary reagents, which limits practical application in industrial chemistry. In order to mitigate these limitations, substantial efforts have been made develop chromium-catalytic approaches. However, excess metal reductants or expensive photocatalysts played essential roles during catalytic cycles. Here, we present a photoactive electron donor-acceptor (EDA) complex-induced chromium-catalyzed route accomplishing alkyl addition aldehydes without requirement photocatalysts. Furthermore, based on pH-dependent site-selective hydrogen isotope exchange (HIE) thianthrenium diversities of β-deuterated secondary could be prepared with high efficiency excellent deuterium incorporation. Mechanistic studies revealed that photo-induced intramolecular single transfer (SET) EDA complex happened provide radicals are captured by Cr(II) species facilitate subsequent Meanwhile, excited Hantzsch ester act as terminal reductant turnover catalyst.

Язык: Английский

Процитировано

1

Deuterated-Alkylation Reagents based on Sulfonium Salts as Cation and Radical Sources DOI

Kazuho Ban,

Jin Tokunaga,

Sota Yoshimura

и другие.

Bulletin of the Chemical Society of Japan, Год журнала: 2024, Номер 97(11)

Опубликована: Окт. 21, 2024

Abstract The replacement of C–H bonds with more stable C–D at the α-position heteroatoms, which is typical metabolic site for cytochrome P450, important in drug discovery. Recently, we have developed dn (deuterated)-alkylated sulfonium salts (1a-dn), were easily prepared by deuteration (H/D exchange reaction) D2O corresponding alkyl diphenylsulfonium (1a), as electrophilic dn-alkylating reagents (cation sources). Herein, newly report an improved preparation method 1a and one-pot synthesis dn-alkylated compounds via subsequent nucleophilic substitution under basic conditions. Additionally, dn-alkyl thianthrenium (1b-dn) also found to work Furthermore, 1b-dn served radical sources photo-induced reaction conditions Ir photocatalyst, Hantzsch ester, or triphenylamine obtain various regioselectively deuterium-incorporated compounds. These will contribute advance

Язык: Английский

Процитировано

1

Pyrrolylsulfonium salts: stable, accessible and versatile pseudohalides for Stille couplings DOI Creative Commons
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.

Язык: Английский

Процитировано

0