Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 365, Issue 11, Pages 1770-1776Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300131
Keywords
C-H activation; regioselective annulation; enaminones; naphtho pyrans; 4-hydroxy alkynoates
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The Rh-catalyzed C-H activation of arenes for oxidative annulations with alkynes is an efficient method to form polycyclic scaffolds. In this study, a regioselective triple annulation of enaminones with hydroxyl-alkynoates via double C-H functionalization was achieved by rhodium catalysis, resulting in polycyclic naphtho-pyran scaffolds. The regioselectivity was controlled by the secondary coordination of hydroxyl group in alkynoate.
Rh-catalyzed C-H activation of arenes for oxidative annulations with alkynes stands out as a protocol for polycyclic scaffolds. This perspective drives us to disclose herein a rhodium catalyzed regioselective triple annulation of enaminones with hydroxyl-alkynoates via double C-H functionalization for polycyclic naphtho-pyran scaffolds. Secondary coordination of OH in alkynoate dictated the regioselectivity. Initial lactonization occurred chemoselectively on to enamine part via carbo rhodation followed by reductive elimination. This protocol was scalable and has shown high functionality tolerance. KIE studies were done to get insight in to the mechanism, and some downstream transformations were achieved to show the synthetic potential of the method.
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