EconPapers    
Economics at your fingertips  
 

Hydroxylamine-mediated C–C amination via an aza-hock rearrangement

Tao Wang, Philipp M. Stein, Hongwei Shi, Chao Hu, Matthias Rudolph and A. Stephen K. Hashmi ()
Additional contact information
Tao Wang: Organisch-Chemisches Institut, Heidelberg University
Philipp M. Stein: Organisch-Chemisches Institut, Heidelberg University
Hongwei Shi: Organisch-Chemisches Institut, Heidelberg University
Chao Hu: Organisch-Chemisches Institut, Heidelberg University
Matthias Rudolph: Organisch-Chemisches Institut, Heidelberg University
A. Stephen K. Hashmi: Organisch-Chemisches Institut, Heidelberg University

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Despite the widespread use of anilines, synthetic challenges to these targets still exist. Selectivity is often an issue, when using the traditional nitration-reduction sequence or more modern approaches, including arene C–H aminations catalyzed by transition metals, photosensitizers, or electrodes. Accordingly, there is still a need for general methods to rapidly, directly access specific isomers of substituted anilines. Here, we report a simple route towards the synthesis of such motifs starting from benzyl alcohols, which are converted to anilines by the use of arylsulfonyl hydroxylamines, via an aza-Hock rearrangement. Good to excellent yields are observed. The method is applicable to various benzyl alcohol surrogates (such as ethers, esters, and halides) as well as simple alkylarenes. Functionalizations of pharmaceutically relevant structures are feasible under the reaction conditions. Over ten amination reagents can be used, which facilitates the rapid assembly of a vast set of compounds.

Date: 2021
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-021-27271-y Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-27271-y

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-021-27271-y

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().

 
Page updated 2025-03-19
Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-27271-y