Herein, we report a protocol for
the stereoselective C–H
alkenylation of five-membered heteroarenes including pyrroles (containing
free NH pyrrole), thiophenes, and furans with 1,3-dithiane derivatives
through dual 1,3-sulfur rearrangements. The site-selective and regioselective
alkenylation of the five-membered heteroarenes proceeded in good yields
via vinyl thionium ions to produce C2 or C5 Heck-type products, respectively.
Methods for the modification of indole
derivatives are
powerful
techniques in organic, medicinal, and biomolecular chemistry. Here,
we report a protocol for the C–H alkenylation of N–H
indoles with β-chlorovinyl dithianes to furnish alkenyl indoles
through dual 1,3-sulfur rearrangements. This alkenylation protocol
could selectively prepare a variety of vinyl indoles in moderate to
high yields with excellent functional group tolerance.
A simple and efficient method for structurally diverse
symmetrical
and unsymmetrical 3,3′- and 2,3′-bisindolylmethanes
has been developed through a one-pot sequential reaction using 1,3-dithiane
as the methylene source. The important AhR agonists ICZ and malassezin
were synthesized with excellent efficiency by this straightforward
approach.
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