Photoinduced Intermolecular Radical Hydroalkylation of Olefins via Ligated Boryl Radicals-Mediated Halogen Atom Transfer

被引：11

作者：

Wan, Ting ^{[1
,2
]}

Ciszewski, Lukasz W. ^{[1
,3
]}

Ravelli, Davide ^{[4
]}

Capaldo, Luca ^{[1
,5
]}

机构：

[1] Univ Amsterdam, vant Hoff Inst Mol Sci HIMS, Flow Chem Grp, NL-1098 XH Amsterdam, Netherlands

[2] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai 201203, Peoples R China

[3] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

[4] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy

[5] Univ Parma, SynCat Lab, Dept Chem Life Sci & Environm Sustainabil, I-43124 Parma, Italy

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 27期

关键词：

AMINOALKYL RADICALS; BORANE COMPLEXES; ALKYL-HALIDES; TRANSFER XAT; CATALYSIS; ACTIVATION; GENERATION; MERGER; TIN;

D O I：

10.1021/acs.orglett.4c02034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Light-mediated Halogen-Atom Transfer (XAT) has become a significant methodology in contemporary synthesis. Unlike alpha-aminoalkyl and silyl radicals, ligated boryl radicals (LBRs) have not been extensively explored as halogen atom abstractors. In this study, we introduce NHC-ligated boranes as optimal radical chain carriers for the intermolecular reductive radical hydroalkylation and hydroarylation of electron-deficient olefins by using direct UV-A light irradiation. DFT analysis allowed us to rationalize the critical role of the NHC ligand in facilitating efficient chain propagation.

引用

页码：5839 / 5843

页数：5

共 50 条

[41] From Styrenes to Fluorinated Benzyl Bromides: A Photoinduced Difunctionalization via Atom Transfer Radical Addition
Granados, Albert
Dhungana, Roshan K.
Sharique, Mohammed
Majhi, Jadab
Molander, Gary A.
ORGANIC LETTERS, 2022, 24 (26) : 4750 - 4755
[42] Free radical polymerization initiated via photoinduced intermolecular electron transfer process: kinetic study 3
Kabatc, J
Kucybala, Z
Pietrzak, M
Scigalski, F
Paczkowski, J
POLYMER, 1999, 40 (03) : 735 - 745
[43] Air Induced Phosphoryl Radical Mediated Stereoselective Hydrosulfonylation of Alkynes via Halogen Atom Transfer: Ingress of Z-Vinyl Sulfones
Tiwari, Shashikant
Kumari, Manisha
Rawat, Diwan S.
ORGANIC LETTERS, 2024, 26 (11) : 2303 - 2308
[44] Visible-light-induced alkyl-arylation of olefins via a halogen-atom transfer process
Ren, Juan
Xia, Xiao-Feng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (31) : 6370 - 6375
[45] Biocompatible polymers via aqueous electrochemically mediated atom transfer radical polymerization
Michieletto, Alessandro
Lorandi, Francesca
De Bon, Francesco
Isse, Abdirisak Ahmed
Gennaro, Armando
JOURNAL OF POLYMER SCIENCE, 2020, 58 (01) : 114 - 123
[46] Synthesis of Polymer Bioconjugates via Photoinduced Atom Transfer Radical Polymerization under Blue Light Irradiation
Fu, Liye
Wang, Zhenhua
Lathwal, Sushil
Enciso, Alan E.
Simakova, Antonina
Das, Subha R.
Russell, Alan J.
Matyjaszewski, Krzysztof
ACS MACRO LETTERS, 2018, 7 (10) : 1248 - 1253
[47] Switchable Radical Polymerization of α-Olefins via Remote Hydrogen Atom or Group Transfer for Enhanced Battery Performance
Song, Silin
Wang, Shuo
Wang, Ziqiang
Sun, Hao
Wang, Xianjin
Zhu, Chen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (06)
[48] Visible-Light-Induced Intermolecular Atom-Transfer Radical Addition of Benzyl Halides to Olefins: Facile Synthesis of Tetrahydroquinolines
Paria, Suva
Pirtsch, Michael
Kais, Viktor
Reiser, Oliver
SYNTHESIS-STUTTGART, 2013, 45 (19): : 2689 - 2698
[49] Copper Makes the Difference: Visible Light-Mediated Atom Transfer Radical Addition Reactions of Iodoform with Olefins
Engl, Sebastian
Reiser, Oliver
ACS CATALYSIS, 2020, 10 (17) : 9899 - 9906
[50] Rose bengal-mediated photoinduced atom transfer radical polymerization for high sensitivity detection of target DNA
Hu, Yaodong
Yu, Shuaibing
Ma, Nan
Kong, Jinming
Zhang, Xueji
TALANTA, 2023, 254

← 1 2 3 4 5 →