Journal
NATURE CHEMISTRY
Volume 8, Issue 12, Pages 1144-1151Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2602
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Funding
- National Science Foundation [CHE-1301409, RII-1330840]
- North Dakota Experimental Program to Stimulate Competitive Research (ND EPSCoR) [EPS-0447679]
- US Department of Energy [DE-AC02-05CH11231]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1301409] Funding Source: National Science Foundation
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Regioselective activation of aromatic C-H bonds is a long-standing challenge for arene functionalization reactions such as the hydroarylation of alkynes. One possible solution is to employ a removable directing group that activates one of several aromatic C-H bonds. Here we report a new catalytic method for regioselective alkyne hydroarylation with benzoic acid derivatives during which the carboxylate functionality directs the alkyne to the ortho-C-H bond with elimination in situ to form a vinylarene product. The decarboxylation stage of this tandem sequence is envisioned to proceed with the assistance of an ortho-alkenyl moiety, which is formed by the initial alkyne coupling. This ruthenium-catalysed decarboxylative alkyne hydroarylation eliminates the common need for pre-existing ortho-substitution on benzoic acids for substrate activation, proceeds under redox-neutral and relatively mild conditions, and tolerates a broad range of synthetically useful aromatic functionality. Thus, it significantly increases the synthetic utility of benzoic acids as easily accessible aromatic building blocks.
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