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. 2011 Jun 17;67(24):4306-4312.
doi: 10.1016/j.tet.2011.04.011.

Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates

Julian M W Chan  1 , Giovanni W Amarante, F Dean Toste
Affiliations

Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates

Julian M W Chan et al. Tetrahedron. .

Abstract

A tandem gold-catalyzed cycloisomerization/Suzuki cross coupling sequence involving arylethynyl-N-methyliminodiacetic acid boronates is described. Combining the mildness of homogeneous gold catalysis with the versatility of N-methyliminodiacetic acid (MIDA) boronates, this tandem two-step method enables the rapid assembly of various aryl-substituted heterocycles without having to isolate or purify any heterocyclic MIDA boronate intermediates. Another major advantage of this method is that a wide range of heterocycles bearing different aryl groups may be made from a single MIDA boronate alkyne precursor.

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Figures

Scheme 1
Scheme 1
Tandem process for the rapid construction of 2-substituted heterocycles.
Scheme 2
Scheme 2
Gold-catalyzed cycloisomerizations of MIDA-alkynylboronates.
Scheme 3
Scheme 3
Regioselective formation of phthalan and isochromene using complementary methods.
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