Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)

Vladimir Kogan; Miriam M. Quintal; Ronny Neumann

doi:10.1021/ol052025e

Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)₂(H₂O)₂] ²⁺ (dmp = 2,9-dimethylphenanthroline)

Vladimir Kogan
, Miriam M. Quintal
, Ronny Neumann^*

^*Corresponding author for this work

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

104 Scopus citations

Abstract

(Chemical Equation Presented) [cis-Ru(II)(dmp)₂(H ₂O)₂]²⁺ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.

Original language	English
Pages (from-to)	5039-5042
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	22
DOIs	https://doi.org/10.1021/ol052025e
State	Published - 27 Oct 2005
Externally published	Yes

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@article{fcd1772808634f24b7f828695a2ded29,

title = "Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)",

abstract = "(Chemical Equation Presented) [cis-Ru(II)(dmp)2(H 2O)2]2+ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.",

author = "Vladimir Kogan and Quintal, \{Miriam M.\} and Ronny Neumann",

year = "2005",

month = oct,

day = "27",

doi = "10.1021/ol052025e",

language = "אנגלית",

volume = "7",

pages = "5039--5042",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)₂(H₂O)₂] ²⁺ (dmp = 2,9-dimethylphenanthroline). / Kogan, Vladimir; Quintal, Miriam M.; Neumann, Ronny.
In: Organic Letters, Vol. 7, No. 22, 27.10.2005, p. 5039-5042.

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

TY - JOUR

T1 - Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)

AU - Kogan, Vladimir

AU - Quintal, Miriam M.

AU - Neumann, Ronny

PY - 2005/10/27

Y1 - 2005/10/27

N2 - (Chemical Equation Presented) [cis-Ru(II)(dmp)2(H 2O)2]2+ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.

AB - (Chemical Equation Presented) [cis-Ru(II)(dmp)2(H 2O)2]2+ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.

UR - https://www.scopus.com/pages/publications/27644509225

U2 - 10.1021/ol052025e

DO - 10.1021/ol052025e

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AN - SCOPUS:27644509225

SN - 1523-7060

VL - 7

SP - 5039

EP - 5042

JO - Organic Letters

JF - Organic Letters

IS - 22