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Synthesis
DOI: 10.1055/a-2353-1722
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Mg-Mediated Regioselective Additions of Bromoform to Quinone Methides and Aurone-derived Azadienes

Deepak Kumar
1   Chemistry, Indian Institute of Technology Bombay, Mumbai, India
,
Nishikant Satam
1   Chemistry, Indian Institute of Technology Bombay, Mumbai, India
,
Irishi N Namboothiri 
2   Chemistry, Indian Institute of Technology Bombay, Mumbai, India
› Author AffiliationsSupported by: Science and Engineering Research Board RD/0120-SERB000-009
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The magnesium-mediated addition of bromoform to conjugated electron-deficient alkenes and imines such as para-quinone methides (p-QMs) and aurone-derived azadienes, respectively, is reported here for the first time. While p-QMs undergo exclusive and hitherto unreported 1,6-addition of bromoform to afford benzylic tribromomethylated diarylmethanes, aurone-derived azadienes undergo both 1,2- and 1,4-additions to furnish α- and -tribromomethylamines. A mechanism involving intermediacy of tribromomethyl radical has been proposed based on control experiments and EPR studies. Representative synthetic transformations have also been carried out.



Publication History

Received: 21 May 2024

Accepted after revision: 26 June 2024

Accepted Manuscript online:
26 June 2024

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