Mild catalytic deoxygenation of amides promoted by thorium metallocene

Sayantani Saha; Moris S. Eisen

doi:10.1039/d0dt02770g

Mild catalytic deoxygenation of amides promoted by thorium metallocene

Sayantani Saha, Moris S. Eisen^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

The organoactinide-catalyzed (Cp*₂ThMe₂) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*₂ThMe₂is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.

Original language	English
Pages (from-to)	12835-12841
Number of pages	7
Journal	Dalton Transactions
Volume	49
Issue number	36
DOIs	https://doi.org/10.1039/d0dt02770g
State	Published - 28 Sep 2020
Externally published	Yes

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title = "Mild catalytic deoxygenation of amides promoted by thorium metallocene",

abstract = "The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.",

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T1 - Mild catalytic deoxygenation of amides promoted by thorium metallocene

AU - Saha, Sayantani

AU - Eisen, Moris S.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2020.

PY - 2020/9/28

Y1 - 2020/9/28

N2 - The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.

AB - The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.

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JO - Dalton Transactions

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Mild catalytic deoxygenation of amides promoted by thorium metallocene

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