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

Ross McLellan; Alan R. Kennedy; Samantha A. Orr; Stuart D. Robertson; Robert E. Mulvey

doi:10.1002/anie.201610905

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

Ross McLellan, Alan R. Kennedy, Samantha A. Orr, Stuart D. Robertson, Robert E. Mulvey

Pure And Applied Chemistry

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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.

Original language	English
Pages (from-to)	1036-1041
Number of pages	6
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	4
Early online date	21 Dec 2016
DOIs	https://doi.org/10.1002/anie.201610905
Publication status	Published - 19 Jan 2017

Keywords

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

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McLellan-etal-ACIE2016-Lithium-dihydropyridine-dehydrogenation-catalysisFinal published version, 1.03 MBLicence: CC BY 4.0

Cite this

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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 = jan,

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doi = "10.1002/anie.201610905",

language = "English",

volume = "56",

pages = "1036--1041",

journal = "Angewandte Chemie International Edition",

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TY - JOUR

T1 - Lithium dihydropyridine dehydrogenation catalysis

T2 - a group 1 approach to cyclisation of diamine-boranes

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

SN - 1433-7851

VL - 56

SP - 1036

EP - 1041

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 4

ER -

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

Abstract

Keywords

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Stuart Robertson

Activated Anionic Aluminium for Synthetic Design, Catalytic and Energy Storage Applications

EPSRC Doctoral Training Grant - DTA, University of Strathclyde | Orr, Samantha Alana