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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of N-methoxybenzamides with a
Sivakalai Mayakrishnan1, Masilamani Tamizmani, Naryanan Uma Maheswari
1Organic & Bioorganic Chemistry Laboratory, CSIR-Central Leather Research Institute, Chennai 600020, India. umamaheswari@clri.res.in.
Abstract:
Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.
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