Deuteration of boranes

catalysed versus non-catalysed processes

David J. Nelson, Jonathan D. Egbert, Steven P. Nolan

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A dichotomy in the reactivity of B-H bonds is reported. A bis(N-heterocyclic carbene)-ligated iridium(iii) complex can effect rapid deuteration of boronate esters at room temperature with low catalyst loadings; however, borane and 9-BBN both undergo deuteration in the absence of catalyst, and do not react with the iridium complexes. This is proposed to result from the inductive electron-withdrawing properties of the boronic ester substituents. Deuterated boronic esters can be accessed rapidly at room temperature with only very low loadings of iridium catalyst. 

Original languageEnglish
Pages (from-to)4105-4109
Number of pages5
JournalDalton Transactions
Volume42
Issue number12
Early online date6 Feb 2013
DOIs
Publication statusPublished - 2013
Externally publishedYes

Fingerprint

Boranes
Iridium
Esters
Catalysts
Temperature
Electrons

Keywords

  • dichotomy
  • B–H bonds
  • reactivity
  • bis(N-heterocyclic carbene)-ligated iridium(III) complex
  • rapid deuteration
  • boronate esters
  • room temperature
  • iridium catalyst

Cite this

Nelson, David J. ; Egbert, Jonathan D. ; Nolan, Steven P. / Deuteration of boranes : catalysed versus non-catalysed processes. In: Dalton Transactions. 2013 ; Vol. 42, No. 12. pp. 4105-4109.
@article{6e817a0e4fff43a7b1c5fa3d4928e3fb,
title = "Deuteration of boranes: catalysed versus non-catalysed processes",
abstract = "A dichotomy in the reactivity of B-H bonds is reported. A bis(N-heterocyclic carbene)-ligated iridium(iii) complex can effect rapid deuteration of boronate esters at room temperature with low catalyst loadings; however, borane and 9-BBN both undergo deuteration in the absence of catalyst, and do not react with the iridium complexes. This is proposed to result from the inductive electron-withdrawing properties of the boronic ester substituents. Deuterated boronic esters can be accessed rapidly at room temperature with only very low loadings of iridium catalyst. ",
keywords = "dichotomy , B–H bonds, reactivity , bis(N-heterocyclic carbene)-ligated iridium(III) complex, rapid deuteration, boronate esters, room temperature, iridium catalyst",
author = "Nelson, {David J.} and Egbert, {Jonathan D.} and Nolan, {Steven P.}",
year = "2013",
doi = "10.1039/c3dt33045a",
language = "English",
volume = "42",
pages = "4105--4109",
journal = "Dalton Transactions",
issn = "1477-9226",
number = "12",

}

Deuteration of boranes : catalysed versus non-catalysed processes. / Nelson, David J.; Egbert, Jonathan D.; Nolan, Steven P.

In: Dalton Transactions, Vol. 42, No. 12, 2013, p. 4105-4109.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Deuteration of boranes

T2 - catalysed versus non-catalysed processes

AU - Nelson, David J.

AU - Egbert, Jonathan D.

AU - Nolan, Steven P.

PY - 2013

Y1 - 2013

N2 - A dichotomy in the reactivity of B-H bonds is reported. A bis(N-heterocyclic carbene)-ligated iridium(iii) complex can effect rapid deuteration of boronate esters at room temperature with low catalyst loadings; however, borane and 9-BBN both undergo deuteration in the absence of catalyst, and do not react with the iridium complexes. This is proposed to result from the inductive electron-withdrawing properties of the boronic ester substituents. Deuterated boronic esters can be accessed rapidly at room temperature with only very low loadings of iridium catalyst. 

AB - A dichotomy in the reactivity of B-H bonds is reported. A bis(N-heterocyclic carbene)-ligated iridium(iii) complex can effect rapid deuteration of boronate esters at room temperature with low catalyst loadings; however, borane and 9-BBN both undergo deuteration in the absence of catalyst, and do not react with the iridium complexes. This is proposed to result from the inductive electron-withdrawing properties of the boronic ester substituents. Deuterated boronic esters can be accessed rapidly at room temperature with only very low loadings of iridium catalyst. 

KW - dichotomy

KW - B–H bonds

KW - reactivity

KW - bis(N-heterocyclic carbene)-ligated iridium(III) complex

KW - rapid deuteration

KW - boronate esters

KW - room temperature

KW - iridium catalyst

UR - http://www.scopus.com/inward/record.url?scp=84874422950&partnerID=8YFLogxK

U2 - 10.1039/c3dt33045a

DO - 10.1039/c3dt33045a

M3 - Article

VL - 42

SP - 4105

EP - 4109

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 12

ER -