Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

Katie D. Mulholland; Sangbin Yoon; Christopher C. Rennie; Eleanor K. Sitch; Alasdair I. McKay; Katharina Edkins; Robert M. Edkins

doi:10.1039/D0CC03161E

Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

Katie D. Mulholland, Sangbin Yoon, Christopher C. Rennie, Eleanor K. Sitch, Alasdair I. McKay, Katharina Edkins, Robert M. Edkins

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Abstract

Ir-catalysed borylation of phthalonitrile produces both 4-(Bpin)phthalonitrile (1) and 3,5-bis(Bpin)phthalonitrile (2), which are potential divergent intermediates for the synthesis of functionalized phthalocyanines. To exemplify the utility of 2, we have prepared a series of 3,5-bis-arylphthalonitriles that in turn undergo sterically controlled regioselective cyclotetramization to give previously unknown C4h 1,3,8,10,15,17,22,24-octaarylphthalocyanines.

Original language	English
Pages (from-to)	8452-8455
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	60
Early online date	18 Jun 2020
DOIs	https://doi.org/10.1039/D0CC03161E
Publication status	Published - 4 Aug 2020

Keywords

synthesis
octaarylphthalocyanines
Phthalocyanines (Pcs)

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10.1039/D0CC03161ELicence: CC BY-NC 3.0

Mulholland-etal-CC-2020-Iridium-catalysed-3-5-bis-borylation-of-phthalonitrile-enables-access-to-a-family-of-C4hAccepted author manuscript, 501 KBLicence: CC BY-NC 3.0

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title = "Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines",

abstract = "Ir-catalysed borylation of phthalonitrile produces both 4-(Bpin)phthalonitrile (1) and 3,5-bis(Bpin)phthalonitrile (2), which are potential divergent intermediates for the synthesis of functionalized phthalocyanines. To exemplify the utility of 2, we have prepared a series of 3,5-bis-arylphthalonitriles that in turn undergo sterically controlled regioselective cyclotetramization to give previously unknown C4h 1,3,8,10,15,17,22,24-octaarylphthalocyanines.",

keywords = "synthesis, octaarylphthalocyanines, Phthalocyanines (Pcs)",

author = "Mulholland, {Katie D.} and Sangbin Yoon and Rennie, {Christopher C.} and Sitch, {Eleanor K.} and McKay, {Alasdair I.} and Katharina Edkins and Edkins, {Robert M.}",

year = "2020",

month = aug,

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doi = "10.1039/D0CC03161E",

language = "English",

volume = "56",

pages = "8452--8455",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

AU - Mulholland, Katie D.

AU - Yoon, Sangbin

AU - Rennie, Christopher C.

AU - Sitch, Eleanor K.

AU - McKay, Alasdair I.

AU - Edkins, Katharina

AU - Edkins, Robert M.

PY - 2020/8/4

Y1 - 2020/8/4

N2 - Ir-catalysed borylation of phthalonitrile produces both 4-(Bpin)phthalonitrile (1) and 3,5-bis(Bpin)phthalonitrile (2), which are potential divergent intermediates for the synthesis of functionalized phthalocyanines. To exemplify the utility of 2, we have prepared a series of 3,5-bis-arylphthalonitriles that in turn undergo sterically controlled regioselective cyclotetramization to give previously unknown C4h 1,3,8,10,15,17,22,24-octaarylphthalocyanines.

AB - Ir-catalysed borylation of phthalonitrile produces both 4-(Bpin)phthalonitrile (1) and 3,5-bis(Bpin)phthalonitrile (2), which are potential divergent intermediates for the synthesis of functionalized phthalocyanines. To exemplify the utility of 2, we have prepared a series of 3,5-bis-arylphthalonitriles that in turn undergo sterically controlled regioselective cyclotetramization to give previously unknown C4h 1,3,8,10,15,17,22,24-octaarylphthalocyanines.

KW - synthesis

KW - octaarylphthalocyanines

KW - Phthalocyanines (Pcs)

U2 - 10.1039/D0CC03161E

DO - 10.1039/D0CC03161E

M3 - Article

SN - 1359-7345

VL - 56

SP - 8452

EP - 8455

JO - Chemical Communications

JF - Chemical Communications

IS - 60

ER -

Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

Abstract

Keywords

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