Iron Catalyzed Hydroboration of Aldehydes and Ketones

Sem Raj Tamang; Michael Findlater

doi:10.1021/acs.joc.7b02020

Iron Catalyzed Hydroboration of Aldehydes and Ketones

Sem Raj Tamang, Michael Findlater

Chemistry and Biochemistry

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88 Scopus citations

Abstract

We report an operationally convenient room temperature hydroboration of aldehydes and ketones employing Fe(acac)₃ as precatalyst. The hydroboration of aldehydes and ketones proceeded efficiently at room temperature to yield, after work up, 1° and 2° alcohols; chemoselective hydroboration of aldehydes over ketones is attained under these conditions. We propose a σ-bond metathesis mechanism in which an Fe-H intermediate is postulated to be a key reactive species.

Original language	English
Pages (from-to)	12857-12862
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.7b02020
State	Published - Dec 1 2017

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abstract = "We report an operationally convenient room temperature hydroboration of aldehydes and ketones employing Fe(acac)3 as precatalyst. The hydroboration of aldehydes and ketones proceeded efficiently at room temperature to yield, after work up, 1° and 2° alcohols; chemoselective hydroboration of aldehydes over ketones is attained under these conditions. We propose a σ-bond metathesis mechanism in which an Fe-H intermediate is postulated to be a key reactive species.",

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AB - We report an operationally convenient room temperature hydroboration of aldehydes and ketones employing Fe(acac)3 as precatalyst. The hydroboration of aldehydes and ketones proceeded efficiently at room temperature to yield, after work up, 1° and 2° alcohols; chemoselective hydroboration of aldehydes over ketones is attained under these conditions. We propose a σ-bond metathesis mechanism in which an Fe-H intermediate is postulated to be a key reactive species.

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Iron Catalyzed Hydroboration of Aldehydes and Ketones

Abstract

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