Hydration of Terminal Alkynes with Molecular Iodine: A Mechanistic Investigation

Primary Faculty Mentor’s Name

Karelle Aiken

Proposal Track

Student

Session Format

Poster

Abstract

Our research group has reported that when using 5-oxo-1-alkynes in an iodine-initiated hydration of terminal alkynes under mild and ambient conditions, it can yield methyl ketones. Using molecular iodine under such conditions, in comparison to the traditional use of a metal catalyst, is more novel, inexpensive, and environmentally friendly. Our findings about the mechanism of this reaction have opened the window to developing methodologies for building blocks based on biologically relevant molecules such as furan analogs and α-substituted ketones. Both of these units can be found in pharmaceuticals and naturally occurring compounds. As such, the iodine-initiated hydration warrants further exploration and here-in we report our initial results with iodine-mediated procedures for furan and ketone derivatives.

Location

Concourse/Atrium

Presentation Year

2014

Start Date

11-15-2014 2:55 PM

End Date

11-15-2014 4:10 PM

Publication Type and Release Option

Presentation (Open Access)

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Nov 15th, 2:55 PM Nov 15th, 4:10 PM

Hydration of Terminal Alkynes with Molecular Iodine: A Mechanistic Investigation

Concourse/Atrium

Our research group has reported that when using 5-oxo-1-alkynes in an iodine-initiated hydration of terminal alkynes under mild and ambient conditions, it can yield methyl ketones. Using molecular iodine under such conditions, in comparison to the traditional use of a metal catalyst, is more novel, inexpensive, and environmentally friendly. Our findings about the mechanism of this reaction have opened the window to developing methodologies for building blocks based on biologically relevant molecules such as furan analogs and α-substituted ketones. Both of these units can be found in pharmaceuticals and naturally occurring compounds. As such, the iodine-initiated hydration warrants further exploration and here-in we report our initial results with iodine-mediated procedures for furan and ketone derivatives.