Direct functionalization of the cyclometalated 2-(2′-pyridyl)phenyl ligand bound to iridium(III)

Ka-Man Cheung; Qian-Feng Zhang; Ka-Wang Chan; Michael H.W. Lam; Ian D. Williams; Wa-Hung Leung

doi:10.1016/j.jorganchem.2005.03.013

Direct functionalization of the cyclometalated 2-(2′-pyridyl)phenyl ligand bound to iridium(III)

Ka-Man Cheung
, Qian-Feng Zhang
, Ka-Wang Chan
, Michael H.W. Lam
, Ian D. Williams
, Wa-Hung Leung

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

21 Citations (Scopus)

Abstract

Treatment of [Ir(ppy)₂(μ-Cl)]₂ and [Ir(ppy) ₂(dtbpy)][OTf] (ppy = 2-(2′-pyridyl)phenyl; dtbpy = 4,4′-di-tert-butyl-2,2′-bipyridine; OTf = triflate) with pyridinium tribromide in the presence of Fe powder led to isolation of [Ir(4-Br-ppy)(μ- Br)]₂ (1) and [Ir(4-Br-ppy)₂(dtbpy)][OTf] (2), respectively. Pd-catalyzed cross-coupling of 2 with RB(OH)₂ afforded [Ir(4-R-ppy)₂(dtbpy)][OTf] (R = 4′-FC₆H₄ (3)), 4′-PhC₆H₄ (4), 2′-thienyl (5), 4′-C₆H₄CH₂OH (6). Treatment of 4 with B₂(pin)₂ (pin = pinacolate) afforded [Ir{4-(pin)B-ppy} ₂(dtbpy)][OTf] (7). The alkynyl complexes [Ir(4-PhCC-ppy) ₂(dtbpy)][OTf] (8) and [Ir{4-Me₂(OH)CC-ppy}(4-Br-ppy) (dtbpy)][OTf] (9) were prepared by cross-coupling of 2 with PhCCSnMe₃ and Me₂C(OH)CCH, respectively. Ethynylation of [Ir(fppy) ₂(dtbpy)][OTf] (fppy = 5-formyl-2-(2′-pyridyl)phenyl) with Ohira's reagent MeCOC(N₂)P(O)(OEt)₂ afforded [Ir{5-HCC-ppy}₂(dtbpy)][OTf] (10). The solid-state structures of 2, 5, 7, and 10 have been determined. © 2005 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	2913-2921
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	12
DOIs	https://doi.org/10.1016/j.jorganchem.2005.03.013
Publication status	Published - 15 Jun 2005

Research Keywords

Cross-coupling
Cyclometalated ligand
Functionalization
Iridium(III)

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@article{743b6ebfc25b4b8d8bf74dcdd8582020,

title = "Direct functionalization of the cyclometalated 2-(2′-pyridyl)phenyl ligand bound to iridium(III)",

abstract = "Treatment of [Ir(ppy)2(μ-Cl)]2 and [Ir(ppy) 2(dtbpy)][OTf] (ppy = 2-(2′-pyridyl)phenyl; dtbpy = 4,4′-di-tert-butyl-2,2′-bipyridine; OTf = triflate) with pyridinium tribromide in the presence of Fe powder led to isolation of [Ir(4-Br-ppy)(μ- Br)]2 (1) and [Ir(4-Br-ppy)2(dtbpy)][OTf] (2), respectively. Pd-catalyzed cross-coupling of 2 with RB(OH)2 afforded [Ir(4-R-ppy)2(dtbpy)][OTf] (R = 4′-FC6H4 (3)), 4′-PhC6H4 (4), 2′-thienyl (5), 4′-C6H4CH2OH (6). Treatment of 4 with B2(pin)2 (pin = pinacolate) afforded [Ir\{4-(pin)B-ppy\} 2(dtbpy)][OTf] (7). The alkynyl complexes [Ir(4-PhCC-ppy) 2(dtbpy)][OTf] (8) and [Ir\{4-Me2(OH)CC-ppy\}(4-Br-ppy) (dtbpy)][OTf] (9) were prepared by cross-coupling of 2 with PhCCSnMe3 and Me2C(OH)CCH, respectively. Ethynylation of [Ir(fppy) 2(dtbpy)][OTf] (fppy = 5-formyl-2-(2′-pyridyl)phenyl) with Ohira's reagent MeCOC(N2)P(O)(OEt)2 afforded [Ir\{5-HCC-ppy\}2(dtbpy)][OTf] (10). The solid-state structures of 2, 5, 7, and 10 have been determined. {\textcopyright} 2005 Elsevier B.V. All rights reserved.",

keywords = "Cross-coupling, Cyclometalated ligand, Functionalization, Iridium(III)",

author = "Ka-Man Cheung and Qian-Feng Zhang and Ka-Wang Chan and Lam, \{Michael H.W.\} and Williams, \{Ian D.\} and Wa-Hung Leung",

year = "2005",

month = jun,

day = "15",

doi = "10.1016/j.jorganchem.2005.03.013",

language = "English",

volume = "690",

pages = "2913--2921",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

number = "12",

}

TY - JOUR

T1 - Direct functionalization of the cyclometalated 2-(2′-pyridyl)phenyl ligand bound to iridium(III)

AU - Cheung, Ka-Man

AU - Zhang, Qian-Feng

AU - Chan, Ka-Wang

AU - Lam, Michael H.W.

AU - Williams, Ian D.

AU - Leung, Wa-Hung

PY - 2005/6/15

Y1 - 2005/6/15

N2 - Treatment of [Ir(ppy)2(μ-Cl)]2 and [Ir(ppy) 2(dtbpy)][OTf] (ppy = 2-(2′-pyridyl)phenyl; dtbpy = 4,4′-di-tert-butyl-2,2′-bipyridine; OTf = triflate) with pyridinium tribromide in the presence of Fe powder led to isolation of [Ir(4-Br-ppy)(μ- Br)]2 (1) and [Ir(4-Br-ppy)2(dtbpy)][OTf] (2), respectively. Pd-catalyzed cross-coupling of 2 with RB(OH)2 afforded [Ir(4-R-ppy)2(dtbpy)][OTf] (R = 4′-FC6H4 (3)), 4′-PhC6H4 (4), 2′-thienyl (5), 4′-C6H4CH2OH (6). Treatment of 4 with B2(pin)2 (pin = pinacolate) afforded [Ir{4-(pin)B-ppy} 2(dtbpy)][OTf] (7). The alkynyl complexes [Ir(4-PhCC-ppy) 2(dtbpy)][OTf] (8) and [Ir{4-Me2(OH)CC-ppy}(4-Br-ppy) (dtbpy)][OTf] (9) were prepared by cross-coupling of 2 with PhCCSnMe3 and Me2C(OH)CCH, respectively. Ethynylation of [Ir(fppy) 2(dtbpy)][OTf] (fppy = 5-formyl-2-(2′-pyridyl)phenyl) with Ohira's reagent MeCOC(N2)P(O)(OEt)2 afforded [Ir{5-HCC-ppy}2(dtbpy)][OTf] (10). The solid-state structures of 2, 5, 7, and 10 have been determined. © 2005 Elsevier B.V. All rights reserved.

AB - Treatment of [Ir(ppy)2(μ-Cl)]2 and [Ir(ppy) 2(dtbpy)][OTf] (ppy = 2-(2′-pyridyl)phenyl; dtbpy = 4,4′-di-tert-butyl-2,2′-bipyridine; OTf = triflate) with pyridinium tribromide in the presence of Fe powder led to isolation of [Ir(4-Br-ppy)(μ- Br)]2 (1) and [Ir(4-Br-ppy)2(dtbpy)][OTf] (2), respectively. Pd-catalyzed cross-coupling of 2 with RB(OH)2 afforded [Ir(4-R-ppy)2(dtbpy)][OTf] (R = 4′-FC6H4 (3)), 4′-PhC6H4 (4), 2′-thienyl (5), 4′-C6H4CH2OH (6). Treatment of 4 with B2(pin)2 (pin = pinacolate) afforded [Ir{4-(pin)B-ppy} 2(dtbpy)][OTf] (7). The alkynyl complexes [Ir(4-PhCC-ppy) 2(dtbpy)][OTf] (8) and [Ir{4-Me2(OH)CC-ppy}(4-Br-ppy) (dtbpy)][OTf] (9) were prepared by cross-coupling of 2 with PhCCSnMe3 and Me2C(OH)CCH, respectively. Ethynylation of [Ir(fppy) 2(dtbpy)][OTf] (fppy = 5-formyl-2-(2′-pyridyl)phenyl) with Ohira's reagent MeCOC(N2)P(O)(OEt)2 afforded [Ir{5-HCC-ppy}2(dtbpy)][OTf] (10). The solid-state structures of 2, 5, 7, and 10 have been determined. © 2005 Elsevier B.V. All rights reserved.

KW - Cross-coupling

KW - Cyclometalated ligand

KW - Functionalization

KW - Iridium(III)

UR - https://www.scopus.com/pages/publications/19944416275

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-19944416275&origin=recordpage

U2 - 10.1016/j.jorganchem.2005.03.013

DO - 10.1016/j.jorganchem.2005.03.013

M3 - RGC 21 - Publication in refereed journal

SN - 0022-328X

VL - 690

SP - 2913

EP - 2921

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 12

ER -

Direct functionalization of the cyclometalated 2-(2′-pyridyl)phenyl ligand bound to iridium(III)

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