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Diiodoindium(III) Cation, InI₂⁺, a Potent Yneophile. Generation and Application to Cationic Cyclization by Selective π-activation of C≡C

Diiodoindium(III) Cation, InI₂⁺, a Potent Yneophile. Generation and Application to Cationic Cyclization by Selective π-activation of C≡C

Karavadhi Surendra, E J Corey

J Am Chem Soc. 2014 Aug 6;136(31):10918-20.

PMID: 25095905

Abstract:

The removal of the iodide ion from indium triiodide by means of reactive Ag(I) salts leads to the formation of the highly reactive ligandless cation InI2(+), which is unusual in having two vacant low-lying p-orbitals. This bivalent Lewis acidity leads to an especially high affinity for the two orthogonal π-bonds of carbon-carbon triple bonds. Consequently, the double-coordinating InI2(+) is an especially effective reagent for the selective activation of C≡C and the catalytic initiation of cationic cyclization processes. A number of such reactions are described to demonstrate synthetic utility.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13510355	Indium(III) iodide		13510-35-5	Price

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