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A Highly Active and Air-Stable Ruthenium Complex for the Ambient Temperature Anti-Markovnikov Reductive Hydration of Terminal Alkynes

Mingshuo Zeng, Le Li and Seth B. Herzon*

*Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States, Email: seth.herzonyale.edu

M. Zeng, L. Li, S. B. Herzon, J. Am. Chem. Soc., 2014, 136, 7058-7067.

DOI: 10.1021/ja501738a (free Supporting Information)


Abstract

An air-stable half-sandwich ruthenium complex is a highly active catalyst for the anti-Markovnikov reductive hydration of alkynes, involving the decarboxylation of formic acid, hydration of the alkyne, and hydrogenation of the intermediate aldehyde. A wide array of terminal alkynes are efficiently processed to linear alcohols using as little as 2 mol % of catalyst at ambient temperature.

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Synthesis of 1,3-Amino Alcohols, 1,3-Diols, Amines, and Carboxylic Acids from Terminal Alkynes

M. Zeng, S. B. Herzon, J. Org. Chem., 2015, 80, 8604-8618.

Regioselective Reductive Hydration of Alkynes To Form Branched or Linear Alcohols

L. Li, S. B. Herzon, J. Am. Chem. Soc., 2012, 134, 17376-17378.


Key Words

saturated alcohols, formic acid


ID: J48-Y2014