Hydration of 5-Oxo-1-Alkynes by a One-Pot Oxy-Iodination/Reduction Sequence: Synthesis of Methyl Ketones with Anchimeric Assistance

Author(s): Julia Trossarello, Adegboyega Egunjobi, Whitney J. Morgan, Rayaj Ahamed, Karelle S. Aiken

Journal Name: Current Organic Synthesis

Volume 11 , Issue 3 , 2014


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Abstract:

Methyl ketone derivatives can be accessed from 5-oxo-1-alkynes in an iodine-initiated hydration of the terminal alkynes. Use of molecular iodine in this manner is novel, inexpensive and a greener alternative to the traditional use of transition metal catalysts. Herein, we report the results of a methodology study which sheds light on the underlying mechanism of this new, metal-free reaction. Our findings indicate that the hydration of the alkyne proceeds via an important anchimeric assistance in which the neighboring keto group participates with a 5-exo-dig cyclization.

Keywords: Anchimeric assistance, deiodination, hydration, ketone, metal-free, molecular iodine, terminal alkyne.

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Article Details

VOLUME: 11
ISSUE: 3
Year: 2014
Page: [466 - 470]
Pages: 5
DOI: 10.2174/15701794113106660069
Price: $65

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