Beilstein J. Org. Chem.2011,7, 631–637, doi:10.3762/bjoc.7.74
)-catalyzed reaction of water with o-acetylenyl-substituted phenyldiazoacetates provides 1H-isochromene derivatives in good yields. The reaction follows a catalytic sequence of gold carbene formation/water O–H insertion/alcohol-alkyne cyclization. The gold(I) complex is the only catalyst in each of these
steps.
Keywords: alkyne; carbene O–H insertion; cyclization; diazo compounds; gold catalysis; 1H-isochromene; Introduction
Transition metal carbene complexes are versatile intermediates and can undergo diverse transformations, including X–H (X = C, O, S, N, etc.) insertions, cyclopropanations, ylide
/cyclization cascade by reacting water with o-acetylenyl-substituted phenyldiazoacetates. The reaction affords 1H-isochromene derivatives in good yields (Scheme 1) [31].
Results and Discussion
At the onset of this investigation, o-acetylenyl-substituted phenyldiazoacetate 1a was selected as the model substrate
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Graphical Abstract
Scheme 1:
Gold(I)-catalyzed insertion/cyclization of o-acetylenyl-substituted phenyldiazoacetates providing 1H...