Copper-catalysed bromine atom transfer cyclisation in SDS micelles.

Area of Science:

• Organic Chemistry
• Photochemistry
• Radical Reactions

Background:

• Atom transfer radical cyclisation (ATRC) is a powerful synthetic tool.
• Activating non-activated alkyl bromides for ATRC remains challenging.
• Developing sustainable and efficient ATRC methods is crucial.

Purpose of the Study:

• To develop a novel ATRC method for non-activated alkyl bromides.
• To investigate the use of blue light irradiation and a copper catalyst.
• To explore the role of sodium dodecyl sulfate (SDS) in the reaction.

Main Methods:

• Utilized a catalytic system comprising CuBr2, Me6-TREN, and ascorbic acid.
• Employed blue light irradiation in a carbonate-buffered aqueous SDS solution.
• Investigated the mechanism of C-Br bond activation and cyclisation.

Main Results:

• Successfully achieved ATRC of non-activated alkyl bromides under blue light.
• Demonstrated the beneficial effect of SDS micelles in enhancing the reaction rate.
• Showed that SDS micelles activate the C-Br bond and suppress reductive cyclisation.

Conclusions:

• Developed an efficient and sustainable ATRC method using visible light photocatalysis.
• Highlighted the crucial role of SDS micelles in facilitating the reaction.
• The findings offer a new pathway for the synthesis of cyclic compounds.