Metal-free N-arylation of secondary amides at room temperature

Fredrik Tinnis; Elin Stridfeldt; Helena Lundberg; Hans Adolfsson; Berit Olofsson

doi:10.1021/acs.orglett.5b01079

Metal-free N-arylation of secondary amides at room temperature

Org Lett. 2015 Jun 5;17(11):2688-91. doi: 10.1021/acs.orglett.5b01079. Epub 2015 May 12.

Authors

Fredrik Tinnis¹, Elin Stridfeldt¹, Helena Lundberg¹, Hans Adolfsson¹, Berit Olofsson^{1

2}

Affiliations

¹ †Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
² ‡Stellenbosch Institute for Advanced Study (STIAS), Wallenberg Research Centre at Stellenbosch University, Marais Street, Stellenbosch 7600, South Africa.

PMID: 25966029
DOI: 10.1021/acs.orglett.5b01079

Abstract

The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Benzene Derivatives / chemistry
Hydrocarbons, Acyclic / chemistry*
Iodine / chemistry*
Metals / chemistry*
Molecular Structure
Onium Compounds / chemistry*
Salts / chemistry*
Temperature

Substances

Amides
Benzene Derivatives
Hydrocarbons, Acyclic
Metals
Onium Compounds
Salts
Iodine