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Synlett 2016; 27(07): 969-976
DOI: 10.1055/s-0035-1561248
DOI: 10.1055/s-0035-1561248
synpacts
Selective Activation of Arylboronate or Aryne Reactivity as a Versatile Postfunctionalization Strategy
Authors
Further Information
Publication History
Received: 03 December 2015
Accepted after revision: 21 December 2015
Publication Date:
20 January 2016 (online)
Dedicated to the memory of Professor Richard F. Heck
Abstract
This review discusses the preparation and orthogonal reactivity of boryl ortho-silyl(hetero)aryl triflates as precursors for arynes. These triflates undergo a wide variety of selective reactions of either the boronate or aryne component. Activation of the boronate group affords diverse (hetero)aryne precursors, whereas aryne activation and capture gives previously difficult-to-access arylboronates, all starting from the same set of common starting materials. Thus, the boronate and aryne functionality can be used for their mutual postfunctionalization with unprecedented flexibility.
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To a first approximation, Ir-catalyzed C-H borylation is selective for the least sterically hindered Ar–H bonds in simple arenes. In reality, the regioselectivity of this process is a more complex topic and the subject of several detailed mechanistic studies. For examples, see: