Synthesis and reactivity of the CO2 adducts of amine/bis(2,4,6-tris(trifluoromethyl)phenyl)borane pairs

Zhenpin Lu; Yuwen Wang; Jia Liu; Yue-Jian Lin; Zhen Hua Li; Huadong Wang

doi:10.1021/om4007246

Synthesis and reactivity of the CO₂ adducts of amine/bis(2,4,6-tris(trifluoromethyl)phenyl)borane pairs

Zhenpin Lu, Yuwen Wang, Jia Liu, Yue-Jian Lin, Zhen Hua Li, Huadong Wang

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

28 Citations (Scopus)

Abstract

Frustrated Lewis pairs (FLPs) comprised of bis(2,4,6-tris(trifluoromethyl) phenyl)borane (1) and a secondary amine (such as HNiPr₂ or HNEt ₂) readily react with CO₂ at room temperature to afford ammonium carbamatoborate salts 2. When the reaction was carried out at 80 C, carbamate boryl esters 3 were obtained with release of 1 equiv of H₂. The iPr-substituted carbamate boryl ester 3a can function as an intramolecular FLP to activate H₂, affording ammonium borylformate salt 4a and formamide adduct 5a. Two reaction pathways leading to the formation of 4a and 5a are proposed. © 2013 American Chemical Society.

Original language	English
Pages (from-to)	6753-6758
Journal	Organometallics
Volume	32
Issue number	22
DOIs	https://doi.org/10.1021/om4007246
Publication status	Published - 25 Nov 2013
Externally published	Yes

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title = "Synthesis and reactivity of the CO2 adducts of amine/bis(2,4,6-tris(trifluoromethyl)phenyl)borane pairs",

abstract = "Frustrated Lewis pairs (FLPs) comprised of bis(2,4,6-tris(trifluoromethyl) phenyl)borane (1) and a secondary amine (such as HNiPr2 or HNEt 2) readily react with CO2 at room temperature to afford ammonium carbamatoborate salts 2. When the reaction was carried out at 80 C, carbamate boryl esters 3 were obtained with release of 1 equiv of H2. The iPr-substituted carbamate boryl ester 3a can function as an intramolecular FLP to activate H2, affording ammonium borylformate salt 4a and formamide adduct 5a. Two reaction pathways leading to the formation of 4a and 5a are proposed. {\textcopyright} 2013 American Chemical Society.",

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T1 - Synthesis and reactivity of the CO2 adducts of amine/bis(2,4,6-tris(trifluoromethyl)phenyl)borane pairs

AU - Lu, Zhenpin

AU - Wang, Yuwen

AU - Liu, Jia

AU - Lin, Yue-Jian

AU - Li, Zhen Hua

AU - Wang, Huadong

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

PY - 2013/11/25

Y1 - 2013/11/25

N2 - Frustrated Lewis pairs (FLPs) comprised of bis(2,4,6-tris(trifluoromethyl) phenyl)borane (1) and a secondary amine (such as HNiPr2 or HNEt 2) readily react with CO2 at room temperature to afford ammonium carbamatoborate salts 2. When the reaction was carried out at 80 C, carbamate boryl esters 3 were obtained with release of 1 equiv of H2. The iPr-substituted carbamate boryl ester 3a can function as an intramolecular FLP to activate H2, affording ammonium borylformate salt 4a and formamide adduct 5a. Two reaction pathways leading to the formation of 4a and 5a are proposed. © 2013 American Chemical Society.

AB - Frustrated Lewis pairs (FLPs) comprised of bis(2,4,6-tris(trifluoromethyl) phenyl)borane (1) and a secondary amine (such as HNiPr2 or HNEt 2) readily react with CO2 at room temperature to afford ammonium carbamatoborate salts 2. When the reaction was carried out at 80 C, carbamate boryl esters 3 were obtained with release of 1 equiv of H2. The iPr-substituted carbamate boryl ester 3a can function as an intramolecular FLP to activate H2, affording ammonium borylformate salt 4a and formamide adduct 5a. Two reaction pathways leading to the formation of 4a and 5a are proposed. © 2013 American Chemical Society.

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DO - 10.1021/om4007246

M3 - RGC 21 - Publication in refereed journal

SN - 0276-7333

VL - 32

SP - 6753

EP - 6758

JO - Organometallics

JF - Organometallics

IS - 22

ER -