Lithium dihydropyridine dehydrogenation catalysis: a group 1 approach to cyclisation of diamine-boranes

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

In reactions restricted previously to a ruthenium catalyst, a 1-lithium-2-alkyl-1,2-dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes to cyclic 1,3,2-diazaborolidines, which can in turn be smoothly arylated in good yields. This study establishes the conditions and solvent dependence of the catalysis via NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X-ray crystallographic studies of several model lithio intermediates.
LanguageEnglish
Pages1036-1041
Number of pages6
JournalAngewandte Chemie International Edition
Volume56
Issue number4
Early online date21 Dec 2016
DOIs
Publication statusPublished - 19 Jan 2017

Fingerprint

Boranes
Diamines
Ruthenium
Cyclization
Dehydrogenation
Catalysis
Lithium
Nuclear magnetic resonance
X-Rays
Catalysts
X rays
Monitoring
Experiments
1,4-dihydropyridine

Keywords

  • NMR monitoring
  • X-ray crystallography
  • lithio intermediates
  • catalytic processes
  • solvent dependence
  • catalysts
  • dehydrogenation
  • catalysis
  • dihydropyridine
  • diaminoboranes
  • lithium

Cite this

@article{a0011f5b44c04e8f81a3204e751e5055,
title = "Lithium dihydropyridine dehydrogenation catalysis: a group 1 approach to cyclisation of diamine-boranes",
abstract = "In reactions restricted previously to a ruthenium catalyst, a 1-lithium-2-alkyl-1,2-dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes to cyclic 1,3,2-diazaborolidines, which can in turn be smoothly arylated in good yields. This study establishes the conditions and solvent dependence of the catalysis via NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X-ray crystallographic studies of several model lithio intermediates.",
keywords = "NMR monitoring, X-ray crystallography, lithio intermediates, catalytic processes, solvent dependence, catalysts, dehydrogenation, catalysis, dihydropyridine, diaminoboranes, lithium",
author = "Ross McLellan and Kennedy, {Alan R.} and Orr, {Samantha A.} and Robertson, {Stuart D.} and Mulvey, {Robert E.}",
year = "2017",
month = "1",
day = "19",
doi = "10.1002/anie.201610905",
language = "English",
volume = "56",
pages = "1036--1041",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
number = "4",

}

TY - JOUR

T1 - Lithium dihydropyridine dehydrogenation catalysis

T2 - Angewandte Chemie International Edition

AU - McLellan, Ross

AU - Kennedy, Alan R.

AU - Orr, Samantha A.

AU - Robertson, Stuart D.

AU - Mulvey, Robert E.

PY - 2017/1/19

Y1 - 2017/1/19

N2 - In reactions restricted previously to a ruthenium catalyst, a 1-lithium-2-alkyl-1,2-dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes to cyclic 1,3,2-diazaborolidines, which can in turn be smoothly arylated in good yields. This study establishes the conditions and solvent dependence of the catalysis via NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X-ray crystallographic studies of several model lithio intermediates.

AB - In reactions restricted previously to a ruthenium catalyst, a 1-lithium-2-alkyl-1,2-dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes to cyclic 1,3,2-diazaborolidines, which can in turn be smoothly arylated in good yields. This study establishes the conditions and solvent dependence of the catalysis via NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X-ray crystallographic studies of several model lithio intermediates.

KW - NMR monitoring

KW - X-ray crystallography

KW - lithio intermediates

KW - catalytic processes

KW - solvent dependence

KW - catalysts

KW - dehydrogenation

KW - catalysis

KW - dihydropyridine

KW - diaminoboranes

KW - lithium

UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

UR - http://dx.doi.org/10.15129/3deff0a8-c62d-47c0-94e5-42e4d819241f

U2 - 10.1002/anie.201610905

DO - 10.1002/anie.201610905

M3 - Article

VL - 56

SP - 1036

EP - 1041

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 4

ER -