Hydroboration of Phosphaalkynes by HB(C6F5)2

Lauren E. Longobardi; Timothy Johnstone; Rosalyn Falconer; Chris Russell; Douglas W. Stephan

doi:10.1002/chem.201602860

Hydroboration of Phosphaalkynes by HB(C6F5)2

Lauren E. Longobardi, Timothy Johnstone, Rosalyn Falconer, Chris Russell, Douglas W. Stephan

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Abstract

The hydroboration of phosphaalkynes with Piers’ borane (HB(C6F5)2) generated unusual phosphaalkenylboranes [RCH=PB(C6F5)2]2 that persisted as dimers in both solution and the solid state. These P2B2 heterocycles underwent ring opening when subjected to nucleophiles, such as pyridine and tert-butylisocyanide, to yield monomeric phosphaalkenylborane adducts RCH=PB(C6F5)2 (L). DFT calculations were performed to probe the nature of the interaction of phosphaalkynes with boranes.

Original language	English
Pages (from-to)	12665 – 12669
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	36
DOIs	https://doi.org/10.1002/chem.201602860
Publication status	Published - 3 Aug 2016

Research Groups and Themes

BCS and TECS CDTs

Keywords

heterocycles
hydroboration
phosphaalkene
phosphaalkenylborane
phosphaalkyne

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10.1002/chem.201602860

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This is the accepted author manuscript (AAM). The final published version (version of record) is available online via Wiley at DOI: 10.1002/chem.201602860. Please refer to any applicable terms of use of the publisher.
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Crosby, J. (Principal Investigator)
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Cite this

@article{1f04d6344fa644d1aaa672c500e9a057,

title = "Hydroboration of Phosphaalkynes by HB(C6F5)2",

abstract = "The hydroboration of phosphaalkynes with Piers{\textquoteright} borane (HB(C6F5)2) generated unusual phosphaalkenylboranes [RCH=PB(C6F5)2]2 that persisted as dimers in both solution and the solid state. These P2B2 heterocycles underwent ring opening when subjected to nucleophiles, such as pyridine and tert-butylisocyanide, to yield monomeric phosphaalkenylborane adducts RCH=PB(C6F5)2 (L). DFT calculations were performed to probe the nature of the interaction of phosphaalkynes with boranes.",

keywords = "heterocycles, hydroboration, phosphaalkene, phosphaalkenylborane, phosphaalkyne",

author = "Longobardi, {Lauren E.} and Timothy Johnstone and Rosalyn Falconer and Chris Russell and Stephan, {Douglas W.}",

year = "2016",

month = aug,

day = "3",

doi = "10.1002/chem.201602860",

language = "English",

volume = "22",

pages = "12665 – 12669",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "36",

}

TY - JOUR

T1 - Hydroboration of Phosphaalkynes by HB(C6F5)2

AU - Longobardi, Lauren E.

AU - Johnstone, Timothy

AU - Falconer, Rosalyn

AU - Russell, Chris

AU - Stephan, Douglas W.

PY - 2016/8/3

Y1 - 2016/8/3

N2 - The hydroboration of phosphaalkynes with Piers’ borane (HB(C6F5)2) generated unusual phosphaalkenylboranes [RCH=PB(C6F5)2]2 that persisted as dimers in both solution and the solid state. These P2B2 heterocycles underwent ring opening when subjected to nucleophiles, such as pyridine and tert-butylisocyanide, to yield monomeric phosphaalkenylborane adducts RCH=PB(C6F5)2 (L). DFT calculations were performed to probe the nature of the interaction of phosphaalkynes with boranes.

AB - The hydroboration of phosphaalkynes with Piers’ borane (HB(C6F5)2) generated unusual phosphaalkenylboranes [RCH=PB(C6F5)2]2 that persisted as dimers in both solution and the solid state. These P2B2 heterocycles underwent ring opening when subjected to nucleophiles, such as pyridine and tert-butylisocyanide, to yield monomeric phosphaalkenylborane adducts RCH=PB(C6F5)2 (L). DFT calculations were performed to probe the nature of the interaction of phosphaalkynes with boranes.

KW - heterocycles

KW - hydroboration

KW - phosphaalkene

KW - phosphaalkenylborane

KW - phosphaalkyne

U2 - 10.1002/chem.201602860

DO - 10.1002/chem.201602860

M3 - Article (Academic Journal)

C2 - 27377569

SN - 0947-6539

VL - 22

SP - 12665

EP - 12669

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 36

ER -

Hydroboration of Phosphaalkynes by HB(C6F5)2

Abstract

Research Groups and Themes

Keywords

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