NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation

Danfeng Deng; Bowen Hu; Min Yang; Dafa Chen

doi:10.1021/acs.organomet.8b00359

NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation

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

49 Scopus citations

Abstract

The bidentate ruthenium complex (HO-C₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(CO)₂Cl₂ (2) could transform to a tridentate product (HO-C₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(CO)Cl₂ (3), which further reacted with CH₃ONa in the presence of PPh₃ to convert to two complexes [(OC₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(PPh₃)₂(CO)]Cl^- (4) and [(OC₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(PPh₃)(CO)Cl] (5), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.

Original language	English
Pages (from-to)	2386-2394
Number of pages	9
Journal	Organometallics
Volume	37
Issue number	14
DOIs	https://doi.org/10.1021/acs.organomet.8b00359
State	Published - 23 Jul 2018
Externally published	Yes

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title = "NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation",

abstract = "The bidentate ruthenium complex (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)2Cl2 (2) could transform to a tridentate product (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)Cl2 (3), which further reacted with CH3ONa in the presence of PPh3 to convert to two complexes [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)2(CO)]Cl- (4) and [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)(CO)Cl] (5), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol \% catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.",

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

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

year = "2018",

month = jul,

day = "23",

doi = "10.1021/acs.organomet.8b00359",

language = "英语",

volume = "37",

pages = "2386--2394",

journal = "Organometallics",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation

AU - Deng, Danfeng

AU - Hu, Bowen

AU - Yang, Min

AU - Chen, Dafa

PY - 2018/7/23

Y1 - 2018/7/23

N2 - The bidentate ruthenium complex (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)2Cl2 (2) could transform to a tridentate product (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)Cl2 (3), which further reacted with CH3ONa in the presence of PPh3 to convert to two complexes [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)2(CO)]Cl- (4) and [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)(CO)Cl] (5), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.

AB - The bidentate ruthenium complex (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)2Cl2 (2) could transform to a tridentate product (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)Cl2 (3), which further reacted with CH3ONa in the presence of PPh3 to convert to two complexes [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)2(CO)]Cl- (4) and [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)(CO)Cl] (5), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.

UR - https://www.scopus.com/pages/publications/85050465762

U2 - 10.1021/acs.organomet.8b00359

DO - 10.1021/acs.organomet.8b00359

M3 - 文章

AN - SCOPUS:85050465762

SN - 0276-7333

VL - 37

SP - 2386

EP - 2394

JO - Organometallics

JF - Organometallics

IS - 14

ER -

NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation

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