| Institution: | 1. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 Canada;2. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 Canada
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands;3. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands |
| Abstract: | The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump. |
