Radical Hydroboration and Hydrosilylation of gem-Difluoroalkenes: Synthesis of α-Difluorinated Alkylborons and Alkylsilanes DOI
Xiaozu Liu, E. Lin, Guojun Chen

и другие.

Organic Letters, Год журнала: 2019, Номер 21(20), С. 8454 - 8458

Опубликована: Окт. 10, 2019

A first example of radical hydroboration and hydrosilylation gem-difluoroalkenes using ABIN as the initiator is described. This protocol features good functional group tolerance, operational simplicity, high atom economy, easy scale-up, enabling efficient assembly a wide range α-difluorinated alkylborons alkylsilanes in moderate to excellent yields. The synthetic utility these products demonstrated by further transformation C–B bond C–Si into valuable CF2-containing molecules.

Язык: Английский

Photoinduced Halogen-Atom Transfer by N-Heterocyclic Carbene-Ligated Boryl Radicals for C(sp3)–C(sp3) Bond Formation DOI Creative Commons
Ting Wan, Luca Capaldo, Davide Ravelli

и другие.

Journal of the American Chemical Society, Год журнала: 2022, Номер 145(2), С. 991 - 999

Опубликована: Дек. 30, 2022

Herein, we present a comprehensive study on the use of N-heterocyclic carbene (NHC)-ligated boryl radicals to enable C(sp3)–C(sp3) bond formation under visible-light irradiation via Halogen-Atom Transfer (XAT). The methodology relies an acridinium dye generate boron-centered from corresponding NHC-ligated boranes single-electron transfer (SET) and deprotonation. These subsequently engage with alkyl halides in XAT step, delivering desired nucleophilic radicals. strategy is very mild accommodates broad scope halides, including medicinally relevant compounds biologically active molecules. key role operative reaction mechanism has been elucidated through combination experimental, spectroscopic, computational studies. This stands as significant advancement chemistry radicals, which had long restricted radical reductions, enabling C–C photoredox conditions.

Язык: Английский

Процитировано

54

Radical hydroboration for the synthesis of organoboron compounds DOI
Yee Lin Phang, Ji‐Kang Jin, Feng‐Lian Zhang

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(32), С. 4275 - 4289

Опубликована: Янв. 1, 2024

This review describes the recent research on radical hydroboration, which covers different boron sources including N-heterocyclic carbene borane, bis(pinacolato)diboron and pinacolborane, as well strategies in boryl generation.

Язык: Английский

Процитировано

12

Halogen Atom Transfer-Induced Homolysis of C–F Bonds by the Excited-State Boryl Radical DOI

Jangwoo Koo,

Weonjeong Kim, Byung Hak Jhun

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(33), С. 22874 - 22880

Опубликована: Авг. 2, 2024

A novel reactivity toward C-F bond functionalization has been developed, which could be designated as fluorine atom transfer (FAT). photoexcited state of an

Язык: Английский

Процитировано

11

Synthesis and Suzuki–Miyaura Cross-Coupling of Alkyl Amine-Boranes. A Boryl Radical-Enabled Strategy DOI Creative Commons
Cornelia S. Buettner,

Chiara Stavagna,

Michael J. Tilby

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(34), С. 24042 - 24052

Опубликована: Авг. 13, 2024

Alkyl organoborons are powerful materials for the construction of C(

Язык: Английский

Процитировано

10

Photoredox‐Controlled β‐Regioselective Radical Hydroboration of Activated Alkenes with NHC‐Boranes DOI
Congjun Zhu, Jie Dong,

Xueting Liu

и другие.

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(31), С. 12817 - 12821

Опубликована: Апрель 27, 2020

In this Communication, we report an unprecedented β-regioselective radical inverse hydroboration (compared with ionic hydroboration) of α,β-unsaturated amides NHC-BH3 enabled by photoredox catalysis. Density functional theory (DFT) calculations show that the unique cycle is a key factor to control hydroboration, lowering energy barrier in comparison other pathways. This protocol provides general and convenient route construct wide range structurally diverse β-borylated synthetically useful yields under mild conditions.

Язык: Английский

Процитировано

62

Photocatalytic C–F Bond Borylation of Polyfluoroarenes with NHC-boranes DOI
Peng‐Ju Xia,

Zhipeng Ye,

Yuan‐Zhuo Hu

и другие.

Organic Letters, Год журнала: 2020, Номер 22(5), С. 1742 - 1747

Опубликована: Фев. 13, 2020

The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH3 has been facilely achieved at room temperature via a single-electron-transfer (SET)/radical addition pathway. This new strategy makes full use the advantage photoredox catalysis to generate key boryl radical direct activation B-H bond. Good functional group tolerance and high regioselectivity offer this protocol incomparable advantages in preparing wide array valuable polyfluoroarylboron compounds. Moreover, both computational experimental studies were performed illustrate reaction mechanism.

Язык: Английский

Процитировано

54

Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes DOI
Yao Liu,

Jilin Li,

Xu‐Ge Liu

и другие.

Organic Letters, Год журнала: 2021, Номер 23(5), С. 1891 - 1897

Опубликована: Фев. 16, 2021

Borylated aza-arenes are of great importance in the area organic synthesis. A radical borylative cyclization isocyanoarenes with N-heterocyclic carbene borane (NHC-BH3) under metal-free conditions was developed. The reaction allows efficient assembly several types borylated (phenanthridines, benzothiazoles, etc.), which difficult to access using alternative methods. Mild conditions, a good functional-group tolerance, and generally efficiencies were observed. utility these products is demonstrated, mechanism discussed.

Язык: Английский

Процитировано

46

Photocatalytic generation of ligated boryl radicals from tertiary amine-borane complexes: An emerging tool in organic synthesis DOI Creative Commons
Luca Capaldo, Timothy Noël, Davide Ravelli

и другие.

Chem Catalysis, Год журнала: 2022, Номер 2(5), С. 957 - 966

Опубликована: Апрель 12, 2022

Язык: Английский

Процитировано

32

Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes DOI Creative Commons

Maude Aelterman,

Tony Biremond,

Philippe Jubault

и другие.

Chemistry - A European Journal, Год журнала: 2022, Номер 28(66)

Опубликована: Сен. 6, 2022

Abstract The electrochemical synthesis of fluorinated allyl silanes and boronates was disclosed. addition electrogenerated boryl or silyl radicals onto many α‐trifluoromethyl α‐difluoromethylstyrenes in an undivided cell allowed the formation a large panel synthetically useful gem ‐difluoro γ‐fluoroallyl (64 examples, from 31 % to 95 yield). In addition, scale up reactions under continuous flow showcased using reactor with promising volumetric productivity (688 g.L −1 .h 496 ). Moreover, synthetic utility these building blocks highlighted through versatile transformations. Finally, plausible reaction mechanisms were suggested explain products.

Язык: Английский

Процитировано

32

B2pin2-Mediated Cascade Cyclization/Aromatization Reaction: Facial Access to Functionalized Indolizines DOI
Xiaoning Li,

Zunsheng Chen,

Weiming Chen

и другие.

Organic Letters, Год журнала: 2022, Номер 24(40), С. 7372 - 7377

Опубликована: Сен. 29, 2022

Herein, a B2pin2-mediated radical cascade cyclization/aromatization reaction of enaminone with pyridine is described. This strategy provides practical way for the construction valuable functionalized indolizines under metal-, external oxidant-, and base-free conditions, which could be compatible various kinds functional groups, such as halogen, π-system, heterocycle, ferrocenyl, etc. A preliminary mechanism investigation indicated that pyridine-boryl formed in situ triggered to occur.

Язык: Английский

Процитировано

31