Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Tertiary-Alcohol-Directed Functionalization of Remote C(sp3 )-H Bonds by Sequential Hydrogen Atom and Heteroaryl Migrations.

Literature DB >> 29276816

Tertiary-Alcohol-Directed Functionalization of Remote C(sp³ )-H Bonds by Sequential Hydrogen Atom and Heteroaryl Migrations.

Xinxin Wu¹, Mingyang Wang¹, Leitao Huan¹, Dongping Wang¹, Jinwei Wang¹, Chen Zhu¹.

Abstract

Reported for the first time is a tertiary-alcohol-guided heteroarylation of remote C(sp3 )-H bonds. The mild and direct generation of alkoxyl radicals from alcohols is enabled by visible-light photocatalysis. A remote hydrogen atom and heteroaryl migration sequence are involved in the reaction. Many sensitive groups remain intact in the reaction, thus illustrating wide functional-group compatibility. This protocol provides a practical strategy for the late-stage modification of alkyl ketones.

Entities: Chemical Species

Keywords: C−H activation; electron transfer; heteroaryls; photocatalysis; radicals

Year: 2018 PMID： 29276816 DOI： 10.1002/anie.201709025

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

19 in total

1. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

Authors: Eisuke Ota; Huaiju Wang; Nils Lennart Frye; Robert R Knowles
Journal: J Am Chem Soc Date: 2019-01-15 Impact factor: 15.419

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622

3. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

Authors: Stefan Andrew Harry; Michael Richard Xiang; Eric Holt; Andrea Zhu; Fereshte Ghorbani; Dhaval Patel; Thomas Lectka
Journal: Chem Sci Date: 2022-05-30 Impact factor: 9.969

Review 4. Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Authors: Anthony R Allen; Efrey A Noten; Corey R J Stephenson
Journal: Chem Rev Date: 2021-10-21 Impact factor: 72.087

Review 5. Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors: Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal: Angew Chem Int Ed Engl Date: 2021-07-21 Impact factor: 16.823

Tertiary-Alcohol-Directed Functionalization of Remote C(sp³ )-H Bonds by Sequential Hydrogen Atom and Heteroaryl Migrations.

1. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

3. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

Review 4. Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Review 5. Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

6. Silver-catalyzed remote Csp³-H functionalization of aliphatic alcohols.

7. Remote C-H functionalization using radical translocating arylating groups.

8. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp³)-H bonds.

9. Visible light-induced direct α C-H functionalization of alcohols.

10. Radical Aryl Migration from Boron to Carbon.