Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 12, 2011
Previous Article Next Article

Photoinitiated ambient temperature copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions in the presence of free-radical diazo initiator (AIBN)

Author affiliations

Abstract

The use of UV light in copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions of various (poly)halogenated compounds to highly active alkenes in the presence of AIBN is reported. Radicals generated from photodecomposition of AIBN efficiently regenerated the copper(I) complex at ambient temperature enabling ATRA of CCl4 and CBr4 with catalyst loadings as low as 0.05 mol-%. The desired monoadduct was obtained in lower yields in the ATRA of less active halogenated compounds, which was mostly due to incomplete alkene conversions. Ambient temperature ATRA of CCl4 to various 1,6-dienes followed by sequential ATRC was also performed in the presence of UV light using [CuII(TPMA)Cl][Cl] complex and AIBN. High yields of the 5-exo-trig cyclic product were obtained for all dienes with preferential formation of the cis isomer.

Graphical abstract: Photoinitiated ambient temperature copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions in the presence of free-radical diazo initiator (AIBN)

Back to tab navigation

Article information


Submitted
14 Dec 2010
Accepted
13 Jan 2011
First published
16 Feb 2011

Dalton Trans., 2011,40, 3060-3066
Article type
Paper

Photoinitiated ambient temperature copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions in the presence of free-radical diazo initiator (AIBN)

M. N. C. Balili and T. Pintauer, Dalton Trans., 2011, 40, 3060
DOI: 10.1039/C0DT01764G

Social activity

Search articles by author

Spotlight

Advertisements