Tandem Imine Formation and Alkyne Metathesis Enabled by Catalyst Choice

Andrew J. Greenlee; Heyu Chen; Chloe I. Wendell; Jeffrey S. Moore

doi:10.1021/acs.joc.2c00538

Tandem Imine Formation and Alkyne Metathesis Enabled by Catalyst Choice

Andrew J. Greenlee, Heyu Chen, Chloe I. Wendell, Jeffrey S. Moore

Research output: Contribution to journal › Article › peer-review

Abstract

Three-rung molecular ladder 8 was prepared in one pot via tandem imine condensation and alkyne metathesis. Catalyst VI is demonstrated to successfully engender the metathesis of imine-bearing substrate 7, while catalyst III does not. The susceptibility of catalyst VI to deactivation by hydrolysis and ligand exchange is demonstrated. Assembly and disassembly of ladder 8 in one pot were demonstrated in the presence and absence of a Lewis acid catalyst.

Original language	English (US)
Pages (from-to)	8429-8436
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	87
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.2c00538
State	Published - Jul 1 2022

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.2c00538

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abstract = "Three-rung molecular ladder 8 was prepared in one pot via tandem imine condensation and alkyne metathesis. Catalyst VI is demonstrated to successfully engender the metathesis of imine-bearing substrate 7, while catalyst III does not. The susceptibility of catalyst VI to deactivation by hydrolysis and ligand exchange is demonstrated. Assembly and disassembly of ladder 8 in one pot were demonstrated in the presence and absence of a Lewis acid catalyst.",

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AB - Three-rung molecular ladder 8 was prepared in one pot via tandem imine condensation and alkyne metathesis. Catalyst VI is demonstrated to successfully engender the metathesis of imine-bearing substrate 7, while catalyst III does not. The susceptibility of catalyst VI to deactivation by hydrolysis and ligand exchange is demonstrated. Assembly and disassembly of ladder 8 in one pot were demonstrated in the presence and absence of a Lewis acid catalyst.

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Tandem Imine Formation and Alkyne Metathesis Enabled by Catalyst Choice

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