Anhydride-Additive-Free Nickel-Catalyzed Deoxygenation of Carboxylic Acids to Olefins

Alex John; Marc A. Hillmyer; William B. Tolman

doi:10.1021/acs.organomet.6b00940

Anhydride-Additive-Free Nickel-Catalyzed Deoxygenation of Carboxylic Acids to Olefins

Alex John, Marc A. Hillmyer, William B. Tolman

Chemistry (Twin Cities)

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

30 Scopus citations

Abstract

A nickel-catalyzed route for direct, anhydride-additive-free deoxygenation of fatty acids to the corresponding olefins has been developed. The transformation is catalyzed by simple nickel salts of the type NiX₂ (X = halide, acetate, acetylacetonate), uses PPh₃ as a stoichiometric reductant, and exhibits selectivity for generation of linear α-olefin products. The reaction was rendered cocatalytic in PPh₃ using 1,1,3,3-tetramethyldisiloxane (TMDS) as terminal reductant for the in situ reduction of OPPh₃ and catalytic Cu(OTf)₂

Original language	English (US)
Pages (from-to)	506-509
Number of pages	4
Journal	Organometallics
Volume	36
Issue number	3
DOIs	https://doi.org/10.1021/acs.organomet.6b00940
State	Published - Feb 13 2017

Bibliographical note

Funding Information:
Funding for this work was provided by the Center for Sustainable Polymers at the University of Minnesota, a National Science Foundation (NSF) supported Center for Chemical Innovation (CHE-1413862).

Access

10.1021/acs.organomet.6b00940

OpenUrl availability

Full text

Cite this

@article{c646bb2a56c8422b8945d58db7857a29,

title = "Anhydride-Additive-Free Nickel-Catalyzed Deoxygenation of Carboxylic Acids to Olefins",

abstract = "A nickel-catalyzed route for direct, anhydride-additive-free deoxygenation of fatty acids to the corresponding olefins has been developed. The transformation is catalyzed by simple nickel salts of the type NiX2 (X = halide, acetate, acetylacetonate), uses PPh3 as a stoichiometric reductant, and exhibits selectivity for generation of linear α-olefin products. The reaction was rendered cocatalytic in PPh3 using 1,1,3,3-tetramethyldisiloxane (TMDS) as terminal reductant for the in situ reduction of OPPh3 and catalytic Cu(OTf)2",

author = "Alex John and Hillmyer, {Marc A.} and Tolman, {William B.}",

note = "Funding Information: Funding for this work was provided by the Center for Sustainable Polymers at the University of Minnesota, a National Science Foundation (NSF) supported Center for Chemical Innovation (CHE-1413862).",

year = "2017",

month = feb,

day = "13",

doi = "10.1021/acs.organomet.6b00940",

language = "English (US)",

volume = "36",

pages = "506--509",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Anhydride-Additive-Free Nickel-Catalyzed Deoxygenation of Carboxylic Acids to Olefins

AU - John, Alex

AU - Hillmyer, Marc A.

AU - Tolman, William B.

N1 - Funding Information: Funding for this work was provided by the Center for Sustainable Polymers at the University of Minnesota, a National Science Foundation (NSF) supported Center for Chemical Innovation (CHE-1413862).

PY - 2017/2/13

Y1 - 2017/2/13

N2 - A nickel-catalyzed route for direct, anhydride-additive-free deoxygenation of fatty acids to the corresponding olefins has been developed. The transformation is catalyzed by simple nickel salts of the type NiX2 (X = halide, acetate, acetylacetonate), uses PPh3 as a stoichiometric reductant, and exhibits selectivity for generation of linear α-olefin products. The reaction was rendered cocatalytic in PPh3 using 1,1,3,3-tetramethyldisiloxane (TMDS) as terminal reductant for the in situ reduction of OPPh3 and catalytic Cu(OTf)2

AB - A nickel-catalyzed route for direct, anhydride-additive-free deoxygenation of fatty acids to the corresponding olefins has been developed. The transformation is catalyzed by simple nickel salts of the type NiX2 (X = halide, acetate, acetylacetonate), uses PPh3 as a stoichiometric reductant, and exhibits selectivity for generation of linear α-olefin products. The reaction was rendered cocatalytic in PPh3 using 1,1,3,3-tetramethyldisiloxane (TMDS) as terminal reductant for the in situ reduction of OPPh3 and catalytic Cu(OTf)2

UR - http://www.scopus.com/inward/record.url?scp=85017513618&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85017513618&partnerID=8YFLogxK

U2 - 10.1021/acs.organomet.6b00940

DO - 10.1021/acs.organomet.6b00940

M3 - Article

AN - SCOPUS:85017513618

SN - 0276-7333

VL - 36

SP - 506

EP - 509

JO - Organometallics

JF - Organometallics

IS - 3

ER -

Anhydride-Additive-Free Nickel-Catalyzed Deoxygenation of Carboxylic Acids to Olefins

Abstract

Bibliographical note

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this