Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

Danfeng Deng; Bowen Hu; Ziyu Zhang; Shengkai Mo; Min Yang; Dafa Chen

doi:10.1021/acs.organomet.9b00172

Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

Danfeng Deng
, Bowen Hu
, Ziyu Zhang
, Shengkai Mo
, Min Yang
, Dafa Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering, Harbin Institute of Technology

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

20 Scopus citations

Abstract

Six Cp∗Ir complexes containing NN-bitentate chelate ligands [Cp∗IrCl(C₅H₄CH₂C₅H₃OH)][Cl] (1), [Cp∗IrCl(C₅H₄CH₂C₅H₃O)] (2), [Cp∗IrCl(C₅H₄C₅H₃OH)] [Cl] (3), [Cp∗IrCl(C₅H₄CH₂C₅H₄)][Cl] (4), [Cp∗IrCl(CH₃OC₅H₃CH₂C₅H₃OCH₃)][Cl] (5), and [Cp∗IrCl(CH₃OC₅H₃CH₂C₅H₃OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaO^tBu or NEt₃ via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol % catalyst loading without extra base in methanol at 120 °C and can be further accelerated by adding NR₃·HCl.

Original language	English
Pages (from-to)	2218-2226
Number of pages	9
Journal	Organometallics
Volume	38
Issue number	9
DOIs	https://doi.org/10.1021/acs.organomet.9b00172
State	Published - 13 May 2019
Externally published	Yes

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@article{6fde045445db4a28984282853cd319a1,

title = "Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment",

abstract = "Six Cp∗Ir complexes containing NN-bitentate chelate ligands [Cp∗IrCl(C5H4CH2C5H3OH)][Cl] (1), [Cp∗IrCl(C5H4CH2C5H3O)] (2), [Cp∗IrCl(C5H4C5H3OH)] [Cl] (3), [Cp∗IrCl(C5H4CH2C5H4)][Cl] (4), [Cp∗IrCl(CH3OC5H3CH2C5H3OCH3)][Cl] (5), and [Cp∗IrCl(CH3OC5H3CH2C5H3OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaOtBu or NEt3 via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol \% catalyst loading without extra base in methanol at 120 °C and can be further accelerated by adding NR3·HCl.",

author = "Danfeng Deng and Bowen Hu and Ziyu Zhang and Shengkai Mo and Min Yang and Dafa Chen",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = may,

day = "13",

doi = "10.1021/acs.organomet.9b00172",

language = "英语",

volume = "38",

pages = "2218--2226",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

AU - Deng, Danfeng

AU - Hu, Bowen

AU - Zhang, Ziyu

AU - Mo, Shengkai

AU - Yang, Min

AU - Chen, Dafa

PY - 2019/5/13

Y1 - 2019/5/13

N2 - Six Cp∗Ir complexes containing NN-bitentate chelate ligands [Cp∗IrCl(C5H4CH2C5H3OH)][Cl] (1), [Cp∗IrCl(C5H4CH2C5H3O)] (2), [Cp∗IrCl(C5H4C5H3OH)] [Cl] (3), [Cp∗IrCl(C5H4CH2C5H4)][Cl] (4), [Cp∗IrCl(CH3OC5H3CH2C5H3OCH3)][Cl] (5), and [Cp∗IrCl(CH3OC5H3CH2C5H3OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaOtBu or NEt3 via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol % catalyst loading without extra base in methanol at 120 °C and can be further accelerated by adding NR3·HCl.

AB - Six Cp∗Ir complexes containing NN-bitentate chelate ligands [Cp∗IrCl(C5H4CH2C5H3OH)][Cl] (1), [Cp∗IrCl(C5H4CH2C5H3O)] (2), [Cp∗IrCl(C5H4C5H3OH)] [Cl] (3), [Cp∗IrCl(C5H4CH2C5H4)][Cl] (4), [Cp∗IrCl(CH3OC5H3CH2C5H3OCH3)][Cl] (5), and [Cp∗IrCl(CH3OC5H3CH2C5H3OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaOtBu or NEt3 via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol % catalyst loading without extra base in methanol at 120 °C and can be further accelerated by adding NR3·HCl.

UR - https://www.scopus.com/pages/publications/85065622665

U2 - 10.1021/acs.organomet.9b00172

DO - 10.1021/acs.organomet.9b00172

M3 - 文章

AN - SCOPUS:85065622665

SN - 0276-7333

VL - 38

SP - 2218

EP - 2226

JO - Organometallics

JF - Organometallics

IS - 9

ER -

Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

Abstract

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