ORGN 22

A comparative survey of several aryne precursors showed 2-iodophenyl triflates as superior aryne progenitors at low temperatures in non-polar media.  Taking advantage of this information, we devised a novel “one-pot” tandem approach to polysubstiuted aromatic compounds involving carbocupration and carbozincation of aryne intermediates.  Arynes are rapidly and cleanly generated, regioselectively carbometallated, then quenched with one of several disparate electrophiles, including electrophilic heteroatoms.  An important application of this approach lies in the synthetic accessibility of numerous analogs of biologically active natural products.