Aliphatic and aromatic C-H activation of benzo[h]quinolines by Rh(I). Unique precursor dependent formation of mono-, di- and trinuclear complexes

Hiyam Salem, Gregory Leitus, Linda J W Shimon, Yael Diskin-Posner, David Milstein

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Treatment of 7,8-benzo[h]quinoline (bhq-H, 1) and 10-methyl benzo[h]quinoline (bhq-Me, 3) with [Rh(C2H4) 2(THF)2][BF4] resulted in double C-H activation of aliphatic and aromatic C-H bonds, yielding the Rh(III) complexes 4 and 5, respectively. The structures of 4 and 5 were revealed by X-ray diffraction. The reaction of 1 with two other slightly different rhodium precursors, [Rh(olefin)n(THF)2][BF4] (COE (n = 2), COD (n = 1)), led to completely different products, a dinuclear complex 7 and a trinuclear complex 6, respectively, which were characterized by X-ray diffraction. Complex 6 exhibits a rare linear Rh-Rh-Rh structure. Utilizing excess of 1 with [Rh(COD)(THF)2][BF4] led to the formation of a new product 8 with no C-H bond activation taking place. Additional C-H activation products of 1, cationic and neutral, in the presence of P iPr3 (9a, 9b and 10) are also presented.

Original languageEnglish
Pages (from-to)260-269
Number of pages10
JournalInorganica Chimica Acta
Volume369
Issue number1
DOIs
Publication statusPublished - Apr 15 2011

Fingerprint

quinoline
crack opening displacement
Chemical activation
activation
products
X ray diffraction
Rhodium
Alkenes
rhodium
diffraction
alkenes
Olefins
x rays
benzo(h)quinoline

Keywords

  • 10-Methyl benzo[h]quinolone
  • 7,8-Benzo[h]quinolone
  • C-H bond activation
  • Rhodium complexes
  • Trinuclear complex

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Aliphatic and aromatic C-H activation of benzo[h]quinolines by Rh(I). Unique precursor dependent formation of mono-, di- and trinuclear complexes. / Salem, Hiyam; Leitus, Gregory; Shimon, Linda J W; Diskin-Posner, Yael; Milstein, David.

In: Inorganica Chimica Acta, Vol. 369, No. 1, 15.04.2011, p. 260-269.

Research output: Contribution to journalArticle

@article{8cb85d790c394eae88a7eee7aee9da09,
title = "Aliphatic and aromatic C-H activation of benzo[h]quinolines by Rh(I). Unique precursor dependent formation of mono-, di- and trinuclear complexes",
abstract = "Treatment of 7,8-benzo[h]quinoline (bhq-H, 1) and 10-methyl benzo[h]quinoline (bhq-Me, 3) with [Rh(C2H4) 2(THF)2][BF4] resulted in double C-H activation of aliphatic and aromatic C-H bonds, yielding the Rh(III) complexes 4 and 5, respectively. The structures of 4 and 5 were revealed by X-ray diffraction. The reaction of 1 with two other slightly different rhodium precursors, [Rh(olefin)n(THF)2][BF4] (COE (n = 2), COD (n = 1)), led to completely different products, a dinuclear complex 7 and a trinuclear complex 6, respectively, which were characterized by X-ray diffraction. Complex 6 exhibits a rare linear Rh-Rh-Rh structure. Utilizing excess of 1 with [Rh(COD)(THF)2][BF4] led to the formation of a new product 8 with no C-H bond activation taking place. Additional C-H activation products of 1, cationic and neutral, in the presence of P iPr3 (9a, 9b and 10) are also presented.",
keywords = "10-Methyl benzo[h]quinolone, 7,8-Benzo[h]quinolone, C-H bond activation, Rhodium complexes, Trinuclear complex",
author = "Hiyam Salem and Gregory Leitus and Shimon, {Linda J W} and Yael Diskin-Posner and David Milstein",
year = "2011",
month = "4",
day = "15",
doi = "10.1016/j.ica.2010.12.064",
language = "English",
volume = "369",
pages = "260--269",
journal = "Inorganica Chimica Acta",
issn = "0020-1693",
publisher = "Elsevier BV",
number = "1",

}

TY - JOUR

T1 - Aliphatic and aromatic C-H activation of benzo[h]quinolines by Rh(I). Unique precursor dependent formation of mono-, di- and trinuclear complexes

AU - Salem, Hiyam

AU - Leitus, Gregory

AU - Shimon, Linda J W

AU - Diskin-Posner, Yael

AU - Milstein, David

PY - 2011/4/15

Y1 - 2011/4/15

N2 - Treatment of 7,8-benzo[h]quinoline (bhq-H, 1) and 10-methyl benzo[h]quinoline (bhq-Me, 3) with [Rh(C2H4) 2(THF)2][BF4] resulted in double C-H activation of aliphatic and aromatic C-H bonds, yielding the Rh(III) complexes 4 and 5, respectively. The structures of 4 and 5 were revealed by X-ray diffraction. The reaction of 1 with two other slightly different rhodium precursors, [Rh(olefin)n(THF)2][BF4] (COE (n = 2), COD (n = 1)), led to completely different products, a dinuclear complex 7 and a trinuclear complex 6, respectively, which were characterized by X-ray diffraction. Complex 6 exhibits a rare linear Rh-Rh-Rh structure. Utilizing excess of 1 with [Rh(COD)(THF)2][BF4] led to the formation of a new product 8 with no C-H bond activation taking place. Additional C-H activation products of 1, cationic and neutral, in the presence of P iPr3 (9a, 9b and 10) are also presented.

AB - Treatment of 7,8-benzo[h]quinoline (bhq-H, 1) and 10-methyl benzo[h]quinoline (bhq-Me, 3) with [Rh(C2H4) 2(THF)2][BF4] resulted in double C-H activation of aliphatic and aromatic C-H bonds, yielding the Rh(III) complexes 4 and 5, respectively. The structures of 4 and 5 were revealed by X-ray diffraction. The reaction of 1 with two other slightly different rhodium precursors, [Rh(olefin)n(THF)2][BF4] (COE (n = 2), COD (n = 1)), led to completely different products, a dinuclear complex 7 and a trinuclear complex 6, respectively, which were characterized by X-ray diffraction. Complex 6 exhibits a rare linear Rh-Rh-Rh structure. Utilizing excess of 1 with [Rh(COD)(THF)2][BF4] led to the formation of a new product 8 with no C-H bond activation taking place. Additional C-H activation products of 1, cationic and neutral, in the presence of P iPr3 (9a, 9b and 10) are also presented.

KW - 10-Methyl benzo[h]quinolone

KW - 7,8-Benzo[h]quinolone

KW - C-H bond activation

KW - Rhodium complexes

KW - Trinuclear complex

UR - http://www.scopus.com/inward/record.url?scp=79953840316&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79953840316&partnerID=8YFLogxK

U2 - 10.1016/j.ica.2010.12.064

DO - 10.1016/j.ica.2010.12.064

M3 - Article

AN - SCOPUS:79953840316

VL - 369

SP - 260

EP - 269

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

SN - 0020-1693

IS - 1

ER -