Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity.
(Pinacolato)boryl ortho-silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride-activated (hetero)aryne precursors, for example, as substrates in transition-metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups.
Department of Chemistry-BMC, Uppsala University, Box 576, 75-123 Uppsala (Sweden) http://www.pilarskigroup.org.
Emilien
E
Demory
Department of Chemistry-BMC, Uppsala University, Box 576, 75-123 Uppsala (Sweden) http://www.pilarskigroup.org.
Karthik
K
Devaraj
Department of Chemistry-Ångström Laboratories, Uppsala University, Box 523, 75-120 Uppsala (Sweden).
Andreas
A
Orthaber
School of Chemistry, University of Bristol, Cantock's Close, Clifton, Bristol, BS8 1TS (UK).
Paul J
PJ
Gates
Department of Chemistry-BMC, Uppsala University, Box 576, 75-123 Uppsala (Sweden) http://www.pilarskigroup.org. lukasz.pilarski@kemi.uu.se.
Lukasz T
LT
Pilarski
CH activation; arynes; boron; chemoselectivity; synthetic methods