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Selective nickel- and manganese-catalyzed decarboxylative cross coupling of some α,β-unsaturated carboxylic acids with cyclic ethers.

Zhang JX, Wang YJ, Zhang W, Wang NX, Bai CB, Xing YL, Li YH, Wen JL - Sci Rep (2014)

Bottom Line: A nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers such as tetrahydrofuran and 1, 4-dioxane was developed.Oxyalkylation was achieved when nickel acetate was used as catalyst, while manganese acetate promoted the reaction of alkenylation.

View Article: PubMed Central - PubMed

Affiliation: Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

ABSTRACT
A nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers such as tetrahydrofuran and 1, 4-dioxane was developed. Oxyalkylation was achieved when nickel acetate was used as catalyst, while manganese acetate promoted the reaction of alkenylation.

No MeSH data available.


Functionalization of cyclic ethers.
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f1: Functionalization of cyclic ethers.

Mentions: In many oxidative coupling reactions, precious metals such as Pd and Ru salts were usually employed. Cu and Fe salts were also used as catalysts. In 2013, Pan reported Iron-catalyzed alkenylation of cinnamic acid with cyclic ethers39. Nickel catalyzed oxidative sp3 C-H functionalization has been demonstrated, but few reports of oxidative coupling reactions utilized a manganese catalyst4041. In this paper, we would like to report a nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers with non-noble metal catalysts (Fig. 1). There is an excellent catalytic selectivity in this work: with the same substrates, nickel acetate only gave 2-(1, 4-dioxan-2-yl)-1-phenylethanone derivatives, while manganese acetate only gave (E)-2-styryl- 1, 4-dioxane derivatives. To the best of our knowledge, this is first report that the same reactants produced selective products under different metal catalysts in oxidative sp3 C-H functionalization.


Selective nickel- and manganese-catalyzed decarboxylative cross coupling of some α,β-unsaturated carboxylic acids with cyclic ethers.

Zhang JX, Wang YJ, Zhang W, Wang NX, Bai CB, Xing YL, Li YH, Wen JL - Sci Rep (2014)

Functionalization of cyclic ethers.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4264008&req=5

f1: Functionalization of cyclic ethers.
Mentions: In many oxidative coupling reactions, precious metals such as Pd and Ru salts were usually employed. Cu and Fe salts were also used as catalysts. In 2013, Pan reported Iron-catalyzed alkenylation of cinnamic acid with cyclic ethers39. Nickel catalyzed oxidative sp3 C-H functionalization has been demonstrated, but few reports of oxidative coupling reactions utilized a manganese catalyst4041. In this paper, we would like to report a nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers with non-noble metal catalysts (Fig. 1). There is an excellent catalytic selectivity in this work: with the same substrates, nickel acetate only gave 2-(1, 4-dioxan-2-yl)-1-phenylethanone derivatives, while manganese acetate only gave (E)-2-styryl- 1, 4-dioxane derivatives. To the best of our knowledge, this is first report that the same reactants produced selective products under different metal catalysts in oxidative sp3 C-H functionalization.

Bottom Line: A nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers such as tetrahydrofuran and 1, 4-dioxane was developed.Oxyalkylation was achieved when nickel acetate was used as catalyst, while manganese acetate promoted the reaction of alkenylation.

View Article: PubMed Central - PubMed

Affiliation: Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

ABSTRACT
A nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers such as tetrahydrofuran and 1, 4-dioxane was developed. Oxyalkylation was achieved when nickel acetate was used as catalyst, while manganese acetate promoted the reaction of alkenylation.

No MeSH data available.