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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.


The α-methyl and α-cyano cinnamic acids reacted with 1, 4-dioxane.
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f3: The α-methyl and α-cyano cinnamic acids reacted with 1, 4-dioxane.

Mentions: To expand the scope of these systems, various α, β-unsaturated carboxylic acids were used as substrates. The related products are showed in (Fig. 2) with moderate to good yields by the optimal condition listed. It's noteworthy that substituted α, β-unsaturated carboxylic acids with electron donating group gave better yields (Fig. 2, 3e, 4e), while the reactants with electron withdrawing group gave lower yields (Fig. 2, 3g, 4g). Several α, β-unsaturated carboxylic acids with a substituent containing furan, thiophene and pyridine structure mainly generated alkenyl products with moderate yields (Fig. 2). When cis-cinnamic acid was used as substrate, the product was also (E)-2-styryl-1, 4-dioxane (Fig. 2). It may be that bond rotation emerged during the radical addition process, or the configuration of cis-cinnamic acid changed to trans in the reaction. These phenomena were observed previously for similar reactions in our group42.


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)

The α-methyl and α-cyano cinnamic acids reacted with 1, 4-dioxane.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f3: The α-methyl and α-cyano cinnamic acids reacted with 1, 4-dioxane.
Mentions: To expand the scope of these systems, various α, β-unsaturated carboxylic acids were used as substrates. The related products are showed in (Fig. 2) with moderate to good yields by the optimal condition listed. It's noteworthy that substituted α, β-unsaturated carboxylic acids with electron donating group gave better yields (Fig. 2, 3e, 4e), while the reactants with electron withdrawing group gave lower yields (Fig. 2, 3g, 4g). Several α, β-unsaturated carboxylic acids with a substituent containing furan, thiophene and pyridine structure mainly generated alkenyl products with moderate yields (Fig. 2). When cis-cinnamic acid was used as substrate, the product was also (E)-2-styryl-1, 4-dioxane (Fig. 2). It may be that bond rotation emerged during the radical addition process, or the configuration of cis-cinnamic acid changed to trans in the reaction. These phenomena were observed previously for similar reactions in our group42.

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.