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

16 Citations (SciVal)

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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

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10.1039/C4CC06522K

Published versionFinal published version, 1.69 MBLicence: CC BY

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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",

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doi = "10.1039/C4CC06522K",

language = "English",

volume = "50",

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journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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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

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Simon Lewis

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

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

Abstract

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Simon Lewis

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MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

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