Photochemical stereospecific hydrogenation of a Ru complex with an NAD +/NADH-type ligand

Takashi Fukushima; Etsuko Fujita; James T. Muckerman; Dmitry E. Polyansky; Tohru Wada; Koji Tanaka

doi:10.1021/ic901935u

Photochemical stereospecific hydrogenation of a Ru complex with an NAD ⁺/NADH-type ligand

Takashi Fukushima, Etsuko Fujita, James T. Muckerman, Dmitry E. Polyansky, Tohru Wada, Koji Tanaka

Brookhaven National Laboratory

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

A polypyridylruthenium complex with an NAD⁺/NADH model ligand, [Ru(bpy)₂(pbn)]²⁺ [bpy = 2,2'-bipyridine; pbn = 2-(2-pyridyl)-benzo[b]-1,5-naphthyridine] in a D₂O/CH ₃CN/triethylamine solution, undergoes stereospecific hydrogenation to give Δ-(S)-and Λ-(R)-[Ru(bpy)₂(pbnDD)]²⁺ [pbnDD = 5,10-dideutero-2-(2-pyridyl)benzo-[b]-1,5-naphthyridine] upon visible-light irradiation. This result clearly indicates the pathway via the Π-stacked dimer of the deuterated oneelectron-reduced species. The reduction of [Ru(bpy)₂(pbn)]²⁺ with Na₂S ₂O₄ in D₂O did not afford any stereospecific products. Furthermore, the more sterically crowded Ru complex, [Ru(dmb) ₂(pbn)]²⁺ (dmb = 6,6'-dimethyl-2,2'-bipyridine), did not produce the corresponding pbnDD species upon irradiation.

Original language	English
Pages (from-to)	11510-11512
Number of pages	3
Journal	Inorganic Chemistry
Volume	48
Issue number	24
DOIs	https://doi.org/10.1021/ic901935u
Publication status	Published - Dec 21 2009

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry

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@article{8c168a879cd34d0db18a05defec41569,

title = "Photochemical stereospecific hydrogenation of a Ru complex with an NAD +/NADH-type ligand",

abstract = "A polypyridylruthenium complex with an NAD+/NADH model ligand, [Ru(bpy)2(pbn)]2+ [bpy = 2,2'-bipyridine; pbn = 2-(2-pyridyl)-benzo[b]-1,5-naphthyridine] in a D2O/CH 3CN/triethylamine solution, undergoes stereospecific hydrogenation to give Δ-(S)-and Λ-(R)-[Ru(bpy)2(pbnDD)]2+ [pbnDD = 5,10-dideutero-2-(2-pyridyl)benzo-[b]-1,5-naphthyridine] upon visible-light irradiation. This result clearly indicates the pathway via the Π-stacked dimer of the deuterated oneelectron-reduced species. The reduction of [Ru(bpy)2(pbn)]2+ with Na2S 2O4 in D2O did not afford any stereospecific products. Furthermore, the more sterically crowded Ru complex, [Ru(dmb) 2(pbn)]2+ (dmb = 6,6'-dimethyl-2,2'-bipyridine), did not produce the corresponding pbnDD species upon irradiation.",

author = "Takashi Fukushima and Etsuko Fujita and Muckerman, {James T.} and Polyansky, {Dmitry E.} and Tohru Wada and Koji Tanaka",

year = "2009",

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doi = "10.1021/ic901935u",

language = "English",

volume = "48",

pages = "11510--11512",

journal = "Inorganic Chemistry",

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T1 - Photochemical stereospecific hydrogenation of a Ru complex with an NAD +/NADH-type ligand

AU - Fukushima, Takashi

AU - Fujita, Etsuko

AU - Muckerman, James T.

AU - Polyansky, Dmitry E.

AU - Wada, Tohru

AU - Tanaka, Koji

PY - 2009/12/21

Y1 - 2009/12/21

N2 - A polypyridylruthenium complex with an NAD+/NADH model ligand, [Ru(bpy)2(pbn)]2+ [bpy = 2,2'-bipyridine; pbn = 2-(2-pyridyl)-benzo[b]-1,5-naphthyridine] in a D2O/CH 3CN/triethylamine solution, undergoes stereospecific hydrogenation to give Δ-(S)-and Λ-(R)-[Ru(bpy)2(pbnDD)]2+ [pbnDD = 5,10-dideutero-2-(2-pyridyl)benzo-[b]-1,5-naphthyridine] upon visible-light irradiation. This result clearly indicates the pathway via the Π-stacked dimer of the deuterated oneelectron-reduced species. The reduction of [Ru(bpy)2(pbn)]2+ with Na2S 2O4 in D2O did not afford any stereospecific products. Furthermore, the more sterically crowded Ru complex, [Ru(dmb) 2(pbn)]2+ (dmb = 6,6'-dimethyl-2,2'-bipyridine), did not produce the corresponding pbnDD species upon irradiation.

AB - A polypyridylruthenium complex with an NAD+/NADH model ligand, [Ru(bpy)2(pbn)]2+ [bpy = 2,2'-bipyridine; pbn = 2-(2-pyridyl)-benzo[b]-1,5-naphthyridine] in a D2O/CH 3CN/triethylamine solution, undergoes stereospecific hydrogenation to give Δ-(S)-and Λ-(R)-[Ru(bpy)2(pbnDD)]2+ [pbnDD = 5,10-dideutero-2-(2-pyridyl)benzo-[b]-1,5-naphthyridine] upon visible-light irradiation. This result clearly indicates the pathway via the Π-stacked dimer of the deuterated oneelectron-reduced species. The reduction of [Ru(bpy)2(pbn)]2+ with Na2S 2O4 in D2O did not afford any stereospecific products. Furthermore, the more sterically crowded Ru complex, [Ru(dmb) 2(pbn)]2+ (dmb = 6,6'-dimethyl-2,2'-bipyridine), did not produce the corresponding pbnDD species upon irradiation.

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