English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
 
 
DownloadE-Mail
  Site-selective and versatile aromatic C−H functionalization by thianthrenation

Berger, F., Plutschack, M. B., Riegger, J., Yu, W., Speicher, S., Ho, M., et al. (2019). Site-selective and versatile aromatic C−H functionalization by thianthrenation. Nature, 567(7747), 223-228. doi:10.1038/s41586-019-0982-0.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Berger, Florian1, Author              
Plutschack, Matthew B.1, Author              
Riegger, Julian2, Author              
Yu, Wanwan1, Author              
Speicher, Samira1, Author              
Ho, Matthew1, Author
Frank, Nils1, Author
Ritter, Tobias1, Author              
Affiliations:
1Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              
2Research Group Tredwell, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466692              

Content

show
hide
Free keywords: -
 Abstract: Direct C–H functionalization can quickly increase useful structural and functional molecular complexity1,2,3. Site selectivity can sometimes be achieved through appropriate directing groups or substitution patterns1,2,3,4—in the absence of such functionality, most aromatic C–H functionalization reactions provide more than one product isomer for most substrates1,4,5. Development of a C–H functionalization reaction that proceeds with high positional selectivity and installs a functional group that can serve as a synthetic linchpin for further functionalization would provide access to a large variety of well-defined arene derivatives. Here we report a highly selective aromatic C–H functionalization reaction that does not require a particular directing group or substitution pattern to achieve selectivity, and provides functionalized arenes that can participate in various transformations. We introduce a persistent sulfur-based radical to functionalize complex arenes with high selectivity and obtain thianthrenium salts that are ready to engage in different transformations, via both transition-metal and photoredox catalysis. This transformation differs fundamentally from all previous aromatic C–H functionalization reactions in that it provides direct access to a large number of derivatives of complex small molecules, quickly generating functional diversity with selectivity that is not achievable by other methods.

Details

show
hide
Language(s): eng - English
 Dates: 2018-07-132019-01-232019-03-132019-03-14
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41586-019-0982-0
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Nature
  Abbreviation : Nature
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 567 (7747) Sequence Number: - Start / End Page: 223 - 228 Identifier: ISSN: 0028-0836
CoNE: https://pure.mpg.de/cone/journals/resource/954925427238