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

Authors

Julia Trossarello, Georgia Southern University
Adegboyego Egunjobi, Georgia Southern University
Whitney J. Morgan, Georgia Southern UniversityFollow
Rayaj Ahamed, Georgia Southern UniversityFollow
Karelle Aiken, Georgia Southern UniversityFollow

Document Type

Article

Publication Date

2012

Publication Title

Current Organic Synthesis

DOI

10.2174/15701794113106660069

ISSN

1875-6271

Abstract

Methyl ketone derivatives can be accessed from5-oxo-1-alkynesin 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.

Recommended Citation

Trossarello, Julia, Adegboyego Egunjobi, Whitney J. Morgan, Rayaj Ahamed, Karelle Aiken. 2012. "Hydration of 5-Oxo-1-Alkynes by a One-Pot Oxy-Iodination/Reduction Sequence: Synthesis of Methyl Ketones with Anchimeric Assistance." Current Organic Synthesis, 11 (3): 466-470: Bentham Science Publishers. doi: 10.2174/15701794113106660069 source: http://www.eurekaselect.com/115167/article
https://digitalcommons.georgiasouthern.edu/chem-facpubs/2