Transition-metal catalyzed cross-coupling reactions between organic halides and organometallic reagents are among the most reliable methods for the construction of a carbon-carbon bond. Recently, phenol and its unactivated derivatives, such as esters and carbamates, have emerged as less expensive and more environmentally benign alternatives to aromatic halides and triflates. Despite the progress in such C-O cross-coupling reactions, most of the transformations have relied on the use of organometallic coupling partners, which leaves the issue of stoichiometric metallic wastes.<br/>We have been developing a rhodium catalyzed C-O bond transformation, in particular, using non-organometallic reagents as a coupling partner. Herein, we report on rhodium-catalyzed C-O bond transformation with alcohols as a coupling partner. Propargyl alcohol undergoes a rhodium-catalyzed alkynylation of aryl carbamates <i>via</i> C-O bond cleavage, while a rhodium-catalyzed reductive cleavage of C-O bond proceeds when isopropanol is used.

Rhodium-catalyzed carbon-oxygen bond reduction and alkynylation of aryl carbamates using alcohol

256th National Meeting (2018)

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