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

doi:10.1016/j.ica.2010.12.064

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

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	260-269
Number of pages	10
Journal	Inorganica Chimica Acta
Volume	369
Issue number	1
DOIs	https://doi.org/10.1016/j.ica.2010.12.064
Publication status	Published - Apr 15 2011

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Keywords

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

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

Cite this

Salem, H., Leitus, G., Shimon, L. J. W., Diskin-Posner, Y., & Milstein, D. (2011). Aliphatic and aromatic C-H activation of benzo[h]quinolines by Rh(I). Unique precursor dependent formation of mono-, di- and trinuclear complexes. Inorganica Chimica Acta, 369(1), 260-269. https://doi.org/10.1016/j.ica.2010.12.064

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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.",

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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.

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10.1016/j.ica.2010.12.064