Hydrofunctionalisation of an Aromatic Triphosphabenzene

Rosalyn L. Falconer; Dihao Zeng; Michael Green; Douglas W. Stephan; John E. McGrady; Christopher A. Russell

doi:10.1002/chem.201903229

Hydrofunctionalisation of an Aromatic Triphosphabenzene

Rosalyn L. Falconer
, Dihao Zeng
, Michael Green
, Douglas W. Stephan
, John E. McGrady^*
, Christopher A. Russell

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

3 Citations (Scopus)

236 Downloads (Pure)

Abstract

The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.

Original language	English
Pages (from-to)	12507-12511
Number of pages	5
Journal	Chemistry - A European Journal
Volume	25
Issue number	54
Early online date	15 Aug 2019
DOIs	https://doi.org/10.1002/chem.201903229
Publication status	Published - 25 Sept 2019

Research Groups and Themes

BCS and TECS CDTs
Inorganic & Materials

Keywords

hydrofunctionalisation
hydrosilylation
metal-free synthesis
phosphorus
triphosphabenzene

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10.1002/chem.201903229

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title = "Hydrofunctionalisation of an Aromatic Triphosphabenzene",

abstract = "The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.",

keywords = "hydrofunctionalisation, hydrosilylation, metal-free synthesis, phosphorus, triphosphabenzene",

author = "Falconer, \{Rosalyn L.\} and Dihao Zeng and Michael Green and Stephan, \{Douglas W.\} and McGrady, \{John E.\} and Russell, \{Christopher A.\}",

year = "2019",

month = sep,

day = "25",

doi = "10.1002/chem.201903229",

language = "English",

volume = "25",

pages = "12507--12511",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

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TY - JOUR

T1 - Hydrofunctionalisation of an Aromatic Triphosphabenzene

AU - Falconer, Rosalyn L.

AU - Zeng, Dihao

AU - Green, Michael

AU - Stephan, Douglas W.

AU - McGrady, John E.

AU - Russell, Christopher A.

PY - 2019/9/25

Y1 - 2019/9/25

N2 - The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.

AB - The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.

KW - hydrofunctionalisation

KW - hydrosilylation

KW - metal-free synthesis

KW - phosphorus

KW - triphosphabenzene

UR - https://www.scopus.com/pages/publications/85072211168

U2 - 10.1002/chem.201903229

DO - 10.1002/chem.201903229

M3 - Article (Academic Journal)

C2 - 31414704

AN - SCOPUS:85072211168

SN - 0947-6539

VL - 25

SP - 12507

EP - 12511

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 54

ER -

Hydrofunctionalisation of an Aromatic Triphosphabenzene

Abstract

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Keywords

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