Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2-Hydroxypyridylmethylene Fragment

Danfeng Deng; Bowen Hu; Min Yang; Dafa Chen

doi:10.1021/acs.organomet.8b00575

Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2-Hydroxypyridylmethylene Fragment

Danfeng Deng
, Bowen Hu
, 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

87 Scopus citations

Abstract

Reaction of complex [Cp∗Ir(HOC₅H₃CH₂C₅H₃OH)Cl][Cl] (1) with AgOTf generated the product [Cp∗Ir(HOC₅H₃CH₂C₅H₃OH)(H₂O)][OTf]₂ (2), which was further transformed to the complex [Cp∗Ir(OC₅H₃CH₂C₅H₃O)(H₂O)] (3) in the presence of t-BuONa via -OH deprotonation. Complexes 1-3 exhibited high activity for the methylation of amines and ketones. These C-C and C-N coupling reactions proceeded in air with 1 mol % catalyst loading in the presence of K₂CO₃.

Original language	English
Pages (from-to)	3353-3359
Number of pages	7
Journal	Organometallics
Volume	37
Issue number	19
DOIs	https://doi.org/10.1021/acs.organomet.8b00575
State	Published - 8 Oct 2018
Externally published	Yes

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title = "Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2-Hydroxypyridylmethylene Fragment",

abstract = "Reaction of complex [Cp∗Ir(HOC5H3CH2C5H3OH)Cl][Cl] (1) with AgOTf generated the product [Cp∗Ir(HOC5H3CH2C5H3OH)(H2O)][OTf]2 (2), which was further transformed to the complex [Cp∗Ir(OC5H3CH2C5H3O)(H2O)] (3) in the presence of t-BuONa via -OH deprotonation. Complexes 1-3 exhibited high activity for the methylation of amines and ketones. These C-C and C-N coupling reactions proceeded in air with 1 mol \% catalyst loading in the presence of K2CO3.",

author = "Danfeng Deng and Bowen Hu and Min Yang and Dafa Chen",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = oct,

day = "8",

doi = "10.1021/acs.organomet.8b00575",

language = "英语",

volume = "37",

pages = "3353--3359",

journal = "Organometallics",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2-Hydroxypyridylmethylene Fragment

AU - Deng, Danfeng

AU - Hu, Bowen

AU - Yang, Min

AU - Chen, Dafa

PY - 2018/10/8

Y1 - 2018/10/8

N2 - Reaction of complex [Cp∗Ir(HOC5H3CH2C5H3OH)Cl][Cl] (1) with AgOTf generated the product [Cp∗Ir(HOC5H3CH2C5H3OH)(H2O)][OTf]2 (2), which was further transformed to the complex [Cp∗Ir(OC5H3CH2C5H3O)(H2O)] (3) in the presence of t-BuONa via -OH deprotonation. Complexes 1-3 exhibited high activity for the methylation of amines and ketones. These C-C and C-N coupling reactions proceeded in air with 1 mol % catalyst loading in the presence of K2CO3.

AB - Reaction of complex [Cp∗Ir(HOC5H3CH2C5H3OH)Cl][Cl] (1) with AgOTf generated the product [Cp∗Ir(HOC5H3CH2C5H3OH)(H2O)][OTf]2 (2), which was further transformed to the complex [Cp∗Ir(OC5H3CH2C5H3O)(H2O)] (3) in the presence of t-BuONa via -OH deprotonation. Complexes 1-3 exhibited high activity for the methylation of amines and ketones. These C-C and C-N coupling reactions proceeded in air with 1 mol % catalyst loading in the presence of K2CO3.

UR - https://www.scopus.com/pages/publications/85053533738

U2 - 10.1021/acs.organomet.8b00575

DO - 10.1021/acs.organomet.8b00575

M3 - 文章

AN - SCOPUS:85053533738

SN - 0276-7333

VL - 37

SP - 3353

EP - 3359

JO - Organometallics

JF - Organometallics

IS - 19

ER -

Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2-Hydroxypyridylmethylene Fragment

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