Metal catalyzed cross coupling and olefin isomerization are synthetically useful and versatile tools in the synthesis of key building blocks. The most crucial challenge is the control of selectivity. Site-selective and sequential cross-couplings of poly(pseudo)halogenated arenes leads to densely functionalized arenes, whereas regio- and stereo-control of an olefin is key for its properties as well as follow up transformations. Metal catalyzed olefin isomerisation often requires dry and inert conditions. In this report, we present a new air-stable PdI dimer, [Pd(µ-I)(PCy2tBu)]2, which enables efficient E-selective olefin migration to enamides and styrene derivatives in air. The presented dimer also triggers rapid and chemoselective C-C functionalization (alkylation and arylation), allowing us to achieve a triply selective sequence of poly(pseudo)halogenated arenes.

Olefin transposition and modular functionalization of arenes in a triply selective sequence enabled by a next generation air-stable palladium(I) dimer in air

ACS Spring Meeting 2021

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