B(C6F5)3: a robust catalyst for the activation of CO2 and dimethylamine borane for the N-formylation reactions

Vitthal B. Saptal; Gaurav Juneja; Bhalchandra M. Bhanage

doi:10.1039/c8nj02816h

B(C₆F₅)₃: a robust catalyst for the activation of CO₂ and dimethylamine borane for the N-formylation reactions

Vitthal B. Saptal, Gaurav Juneja, Bhalchandra M. Bhanage^*

^*Corresponding author for this work

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

30 Scopus citations

Abstract

In this work, B(C₆F₅)₃ is utilized as an organocatalyst for the transition-metal-free N-formylation of amines using carbon dioxide (CO₂) as a C1 source and dimethylamine borane (Me₂NH·BH₃) as a green hydrogen transfer source at 80 °C. Most reported works utilize silane and hydrogen for the N-formylation reactions using CO₂ which have thus far been limited by low atom economy, high cost or the use of harsh reaction conditions. This catalytic protocol affords a broad range of formylated products in moderate to excellent yields under mild reaction conditions with a high TON and TOF. The bulky boron (B(C₆F₅)₃) catalyst reacts with amines and forms a Frustrated Lewis Pair (FLP) and activates CO₂ and Me₂NH·BH₃ molecules. Additionally, this boron catalyst shows high catalytic activity for the cyclization of o-phenylenediamines using CO₂ and Me₂NH·BH₃ to synthesize benzimidazoles.

Original language	English
Pages (from-to)	15847-15851
Number of pages	5
Journal	New Journal of Chemistry
Volume	42
Issue number	19
DOIs	https://doi.org/10.1039/c8nj02816h
State	Published - 2018
Externally published	Yes

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title = "B(C6F5)3: a robust catalyst for the activation of CO2 and dimethylamine borane for the N-formylation reactions",

abstract = "In this work, B(C6F5)3 is utilized as an organocatalyst for the transition-metal-free N-formylation of amines using carbon dioxide (CO2) as a C1 source and dimethylamine borane (Me2NH·BH3) as a green hydrogen transfer source at 80 °C. Most reported works utilize silane and hydrogen for the N-formylation reactions using CO2 which have thus far been limited by low atom economy, high cost or the use of harsh reaction conditions. This catalytic protocol affords a broad range of formylated products in moderate to excellent yields under mild reaction conditions with a high TON and TOF. The bulky boron (B(C6F5)3) catalyst reacts with amines and forms a Frustrated Lewis Pair (FLP) and activates CO2 and Me2NH·BH3 molecules. Additionally, this boron catalyst shows high catalytic activity for the cyclization of o-phenylenediamines using CO2 and Me2NH·BH3 to synthesize benzimidazoles.",

author = "Saptal, {Vitthal B.} and Gaurav Juneja and Bhanage, {Bhalchandra M.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.",

year = "2018",

doi = "10.1039/c8nj02816h",

language = "英语",

volume = "42",

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T2 - a robust catalyst for the activation of CO2 and dimethylamine borane for the N-formylation reactions

AU - Saptal, Vitthal B.

AU - Juneja, Gaurav

AU - Bhanage, Bhalchandra M.

N1 - Publisher Copyright: © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

PY - 2018

Y1 - 2018

N2 - In this work, B(C6F5)3 is utilized as an organocatalyst for the transition-metal-free N-formylation of amines using carbon dioxide (CO2) as a C1 source and dimethylamine borane (Me2NH·BH3) as a green hydrogen transfer source at 80 °C. Most reported works utilize silane and hydrogen for the N-formylation reactions using CO2 which have thus far been limited by low atom economy, high cost or the use of harsh reaction conditions. This catalytic protocol affords a broad range of formylated products in moderate to excellent yields under mild reaction conditions with a high TON and TOF. The bulky boron (B(C6F5)3) catalyst reacts with amines and forms a Frustrated Lewis Pair (FLP) and activates CO2 and Me2NH·BH3 molecules. Additionally, this boron catalyst shows high catalytic activity for the cyclization of o-phenylenediamines using CO2 and Me2NH·BH3 to synthesize benzimidazoles.

AB - In this work, B(C6F5)3 is utilized as an organocatalyst for the transition-metal-free N-formylation of amines using carbon dioxide (CO2) as a C1 source and dimethylamine borane (Me2NH·BH3) as a green hydrogen transfer source at 80 °C. Most reported works utilize silane and hydrogen for the N-formylation reactions using CO2 which have thus far been limited by low atom economy, high cost or the use of harsh reaction conditions. This catalytic protocol affords a broad range of formylated products in moderate to excellent yields under mild reaction conditions with a high TON and TOF. The bulky boron (B(C6F5)3) catalyst reacts with amines and forms a Frustrated Lewis Pair (FLP) and activates CO2 and Me2NH·BH3 molecules. Additionally, this boron catalyst shows high catalytic activity for the cyclization of o-phenylenediamines using CO2 and Me2NH·BH3 to synthesize benzimidazoles.

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VL - 42

SP - 15847

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JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 19

ER -

B(C₆F₅)₃: a robust catalyst for the activation of CO₂ and dimethylamine borane for the N-formylation reactions

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