Catalytic dehalogenation of aryl chlorides mediated by ruthenium(II) phosphine complexes

M E  Cucullu; Steven Patrick Nolan; T R  Belderrain; R H  Grubbs

doi:10.1021/om980682n

Catalytic dehalogenation of aryl chlorides mediated by ruthenium(II) phosphine complexes

M E Cucullu
, Steven Patrick Nolan
, T R Belderrain
, R H Grubbs

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

Abstract

The catalytic dechlorination of aryl chlorides performed by RuHCl(H-2)(2)(PCy3)(2) and RuH2(H-2)(2)(PCy3)(2) in alcohols is rapid and complete within 1 h. The mechanism involves a transfer hydrogenation step with participation of the alcohol. The system exhibits significant functional group tolerance. The catalyst can be generated in situ from [RuCl2(COD)](x) (COD = cyclooctadiene) and 2 equiv of phosphine (PCy3 or (PPr3)-Pr-i). Catalytic conversions are similar to those observed when an isolated precatalyst is used. Mechanistic considerations and the scope of the process are discussed.

Original language	English
Pages (from-to)	1299-1304
Number of pages	6
Journal	Organometallics
Volume	18
Issue number	7
DOIs	https://doi.org/10.1021/om980682n
Publication status	Published - 29 Mar 1999

Keywords

ASYMMETRIC TRANSFER HYDROGENATION
ORGANIC HALIDES
CHIRAL LIGANDS
REDUCTION
HYDROGENOLYSIS
KETONES

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title = "Catalytic dehalogenation of aryl chlorides mediated by ruthenium(II) phosphine complexes",

abstract = "The catalytic dechlorination of aryl chlorides performed by RuHCl(H-2)(2)(PCy3)(2) and RuH2(H-2)(2)(PCy3)(2) in alcohols is rapid and complete within 1 h. The mechanism involves a transfer hydrogenation step with participation of the alcohol. The system exhibits significant functional group tolerance. The catalyst can be generated in situ from [RuCl2(COD)](x) (COD = cyclooctadiene) and 2 equiv of phosphine (PCy3 or (PPr3)-Pr-i). Catalytic conversions are similar to those observed when an isolated precatalyst is used. Mechanistic considerations and the scope of the process are discussed.",

keywords = "ASYMMETRIC TRANSFER HYDROGENATION, ORGANIC HALIDES, CHIRAL LIGANDS, REDUCTION, HYDROGENOLYSIS, KETONES",

author = "Cucullu, \{M E\} and Nolan, \{Steven Patrick\} and Belderrain, \{T R\} and Grubbs, \{R H\}",

year = "1999",

month = mar,

day = "29",

doi = "10.1021/om980682n",

language = "English",

volume = "18",

pages = "1299--1304",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "7",

}

TY - JOUR

T1 - Catalytic dehalogenation of aryl chlorides mediated by ruthenium(II) phosphine complexes

AU - Cucullu, M E

AU - Nolan, Steven Patrick

AU - Belderrain, T R

AU - Grubbs, R H

PY - 1999/3/29

Y1 - 1999/3/29

N2 - The catalytic dechlorination of aryl chlorides performed by RuHCl(H-2)(2)(PCy3)(2) and RuH2(H-2)(2)(PCy3)(2) in alcohols is rapid and complete within 1 h. The mechanism involves a transfer hydrogenation step with participation of the alcohol. The system exhibits significant functional group tolerance. The catalyst can be generated in situ from [RuCl2(COD)](x) (COD = cyclooctadiene) and 2 equiv of phosphine (PCy3 or (PPr3)-Pr-i). Catalytic conversions are similar to those observed when an isolated precatalyst is used. Mechanistic considerations and the scope of the process are discussed.

AB - The catalytic dechlorination of aryl chlorides performed by RuHCl(H-2)(2)(PCy3)(2) and RuH2(H-2)(2)(PCy3)(2) in alcohols is rapid and complete within 1 h. The mechanism involves a transfer hydrogenation step with participation of the alcohol. The system exhibits significant functional group tolerance. The catalyst can be generated in situ from [RuCl2(COD)](x) (COD = cyclooctadiene) and 2 equiv of phosphine (PCy3 or (PPr3)-Pr-i). Catalytic conversions are similar to those observed when an isolated precatalyst is used. Mechanistic considerations and the scope of the process are discussed.

KW - ASYMMETRIC TRANSFER HYDROGENATION

KW - ORGANIC HALIDES

KW - CHIRAL LIGANDS

KW - REDUCTION

KW - HYDROGENOLYSIS

KW - KETONES

U2 - 10.1021/om980682n

DO - 10.1021/om980682n

M3 - Article

SN - 0276-7333

VL - 18

SP - 1299

EP - 1304

JO - Organometallics

JF - Organometallics

IS - 7

ER -

Catalytic dehalogenation of aryl chlorides mediated by ruthenium(II) phosphine complexes

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