Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters

Sem Raj Tamang; Arpita Singh; Deepika Bedi; Adineh Rezaei Bazkiaei; Audrey A. Warner; Keeley Glogau; Corey McDonald; Daniel K. Unruh; Michael Findlater

doi:10.1038/s41929-019-0405-5

Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters

Sem Raj Tamang, Arpita Singh, Deepika Bedi, Adineh Rezaei Bazkiaei, Audrey A. Warner, Keeley Glogau, Corey McDonald, Daniel K. Unruh, Michael Findlater

Chemistry and Biochemistry

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

19 Scopus citations

Abstract

Catalytic reduction of carboxamides into their corresponding amines is an attractive but extremely challenging transformation, which often meets with limited success; the valuable amine products drive ongoing research in this area. Here we show the direct deoxygenation of carboxamides using earth-abundant lanthanum catalysts in the presence of HBpin, presenting good to excellent yields with broad substrate scope and functional group/heteroatom tolerance. Moreover, this method is also effective in catalysing the hydroboration of esters. Finally, selective cleavage of the amide group bonds (C–N versus C–O) could be achieved based on the nature of the nitrogen substituents.

Original language	English
Pages (from-to)	154-162
Number of pages	9
Journal	Nature Catalysis
Volume	3
Issue number	2
DOIs	https://doi.org/10.1038/s41929-019-0405-5
State	Published - Feb 1 2020

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title = "Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters",

abstract = "Catalytic reduction of carboxamides into their corresponding amines is an attractive but extremely challenging transformation, which often meets with limited success; the valuable amine products drive ongoing research in this area. Here we show the direct deoxygenation of carboxamides using earth-abundant lanthanum catalysts in the presence of HBpin, presenting good to excellent yields with broad substrate scope and functional group/heteroatom tolerance. Moreover, this method is also effective in catalysing the hydroboration of esters. Finally, selective cleavage of the amide group bonds (C–N versus C–O) could be achieved based on the nature of the nitrogen substituents.",

author = "Tamang, {Sem Raj} and Arpita Singh and Deepika Bedi and Bazkiaei, {Adineh Rezaei} and Warner, {Audrey A.} and Keeley Glogau and Corey McDonald and Unruh, {Daniel K.} and Michael Findlater",

note = "Funding Information: The authors are grateful to both The National Science Foundation (CHE-1554906) and the Welch Foundation (D-1807) for their financial support. Publisher Copyright: {\textcopyright} 2020, The Author(s), under exclusive licence to Springer Nature Limited.",

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doi = "10.1038/s41929-019-0405-5",

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Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters. / Tamang, Sem Raj; Singh, Arpita; Bedi, Deepika; Bazkiaei, Adineh Rezaei; Warner, Audrey A.; Glogau, Keeley; McDonald, Corey; Unruh, Daniel K.; Findlater, Michael.

In: Nature Catalysis, Vol. 3, No. 2, 01.02.2020, p. 154-162.

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

TY - JOUR

T1 - Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters

AU - Tamang, Sem Raj

AU - Singh, Arpita

AU - Bedi, Deepika

AU - Bazkiaei, Adineh Rezaei

AU - Warner, Audrey A.

AU - Glogau, Keeley

AU - McDonald, Corey

AU - Unruh, Daniel K.

AU - Findlater, Michael

N1 - Funding Information: The authors are grateful to both The National Science Foundation (CHE-1554906) and the Welch Foundation (D-1807) for their financial support. Publisher Copyright: © 2020, The Author(s), under exclusive licence to Springer Nature Limited.

PY - 2020/2/1

Y1 - 2020/2/1

N2 - Catalytic reduction of carboxamides into their corresponding amines is an attractive but extremely challenging transformation, which often meets with limited success; the valuable amine products drive ongoing research in this area. Here we show the direct deoxygenation of carboxamides using earth-abundant lanthanum catalysts in the presence of HBpin, presenting good to excellent yields with broad substrate scope and functional group/heteroatom tolerance. Moreover, this method is also effective in catalysing the hydroboration of esters. Finally, selective cleavage of the amide group bonds (C–N versus C–O) could be achieved based on the nature of the nitrogen substituents.

AB - Catalytic reduction of carboxamides into their corresponding amines is an attractive but extremely challenging transformation, which often meets with limited success; the valuable amine products drive ongoing research in this area. Here we show the direct deoxygenation of carboxamides using earth-abundant lanthanum catalysts in the presence of HBpin, presenting good to excellent yields with broad substrate scope and functional group/heteroatom tolerance. Moreover, this method is also effective in catalysing the hydroboration of esters. Finally, selective cleavage of the amide group bonds (C–N versus C–O) could be achieved based on the nature of the nitrogen substituents.

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JO - Nature Catalysis

JF - Nature Catalysis

SN - 2520-1158

IS - 2

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Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters

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