Experimental and theoretical investigations into the unusual regioselectivity of 4,5-, 5,6-, and 6,7-indole aryne cycloadditions

Ashley N. Garr, Diheng Luo, Neil Brown, Christopher J. Cramer, Keith R. Buszek, David Vandervelde

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

Abstract

"Chemical Equation Presented" The 6,7-indolyne shows remarkable regioselectivity in its cycloaddition with 2-substituted furans. Electron-donating groups give predominantly the more sterically crowded product, while electron-withdrawing groups display the opposite regioselectivity. By contrast, 4,5- and 5,6-indolynes show no regioselectivity. Optimized electronic structure calculations using the M06-2X density functional and 6-311+G(2df,p) basis set revealed that the 6,7-indolynes are highly polar structures and that their cycloadditions have substantial electrophilic substitution character that leads to the observed preference for contrasteric products.

Original languageEnglish (US)
Pages (from-to)96-99
Number of pages4
JournalOrganic Letters
Volume12
Issue number1
DOIs
StatePublished - Jan 1 2010

Fingerprint Dive into the research topics of 'Experimental and theoretical investigations into the unusual regioselectivity of 4,5-, 5,6-, and 6,7-indole aryne cycloadditions'. Together they form a unique fingerprint.

Cite this