Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Catherine L. Lyall; Camilla C. Shotton; Monserrat Pérez-salvia; Dan Pantos; Simon E. Lewis

doi:10.1039/C4CC06522K

Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Catherine L. Lyall, Camilla C. Shotton, Monserrat Pérez-salvia, Dan Pantos, Simon E. Lewis

Research output: Contribution to journal › Article › peer-review

11 Citations (SciVal)

180 Downloads (Pure)

Abstract

We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C–H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of a directed borylation mechanism. Borylated NDIs are substrates for Suzuki–Miyaura couplings and borylation of an NDI bearing two inequivalent N-substituents has also been demonstrated.

Original language	English
Pages (from-to)	13837-13840
Journal	Chemical Communications
Volume	50
Issue number	89
Early online date	18 Sept 2014
DOIs	https://doi.org/10.1039/C4CC06522K
Publication status	Published - 18 Nov 2014

Access to Document

10.1039/C4CC06522K

Published versionFinal published version, 1.69 MBLicence: CC BY

Cite this

@article{2566ad7ac33b43f182242145fcc9827d,

title = "Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation",

abstract = "We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C–H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of a directed borylation mechanism. Borylated NDIs are substrates for Suzuki–Miyaura couplings and borylation of an NDI bearing two inequivalent N-substituents has also been demonstrated.",

author = "Lyall, {Catherine L.} and Shotton, {Camilla C.} and Monserrat P{\'e}rez-salvia and Dan Pantos and Lewis, {Simon E.}",

year = "2014",

month = nov,

day = "18",

doi = "10.1039/C4CC06522K",

language = "English",

volume = "50",

pages = "13837--13840",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "89",

}

TY - JOUR

T1 - Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

AU - Lyall, Catherine L.

AU - Shotton, Camilla C.

AU - Pérez-salvia, Monserrat

AU - Pantos, Dan

AU - Lewis, Simon E.

PY - 2014/11/18

Y1 - 2014/11/18

N2 - We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C–H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of a directed borylation mechanism. Borylated NDIs are substrates for Suzuki–Miyaura couplings and borylation of an NDI bearing two inequivalent N-substituents has also been demonstrated.

AB - We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C–H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of a directed borylation mechanism. Borylated NDIs are substrates for Suzuki–Miyaura couplings and borylation of an NDI bearing two inequivalent N-substituents has also been demonstrated.

UR - http://dx.doi.org/10.1039/C4CC06522K

U2 - 10.1039/C4CC06522K

DO - 10.1039/C4CC06522K

M3 - Article

SN - 1359-7345

VL - 50

SP - 13837

EP - 13840

JO - Chemical Communications

JF - Chemical Communications

IS - 89

ER -

Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Abstract

Access to Document

Other files and links

Fingerprint

Simon Lewis

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

Cite this

Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Abstract

Access to Document

Other files and links

Fingerprint

Profiles

Simon Lewis

Equipment

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

Cite this