Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst

Nitin T. Patil; Isao Kadota; Akinori Shibuya; Soo Gyoung Young; Yoshinori Yamamoto

doi:10.1002/adsc.200404046

Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst

Nitin T. Patil, Isao Kadota, Akinori Shibuya, Soo Gyoung Young, Yoshinori Yamamoto

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

54 Citations (Scopus)

Abstract

We have developed an efficient and ecochemical process for the allylation of carbon pronucleophiles with alkynes. The reaction of alkynes with various active methynes and methylenes in the presence of Pd(PPh₃) ₄/acetic acid gave the corresponding allylated products in high yields and high regioselectivities. In the present catalytic system, the key is the use of carboxylic acid which dramatically enhances the rate of the reactions. One of the important features of this process is that neither a leaving group is liberated nor is a stoichiometric amount of base needed to generate the nucleophiles.

Original language	English
Pages (from-to)	800-804
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	346
Issue number	7
DOIs	https://doi.org/10.1002/adsc.200404046
Publication status	Published - Jul 2004
Externally published	Yes

Keywords

Alkynes
Allylation
C-C bond formation
Carbon nucleophiles
Homogeneous catalysis
Palladium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200404046

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abstract = "We have developed an efficient and ecochemical process for the allylation of carbon pronucleophiles with alkynes. The reaction of alkynes with various active methynes and methylenes in the presence of Pd(PPh3) 4/acetic acid gave the corresponding allylated products in high yields and high regioselectivities. In the present catalytic system, the key is the use of carboxylic acid which dramatically enhances the rate of the reactions. One of the important features of this process is that neither a leaving group is liberated nor is a stoichiometric amount of base needed to generate the nucleophiles.",

keywords = "Alkynes, Allylation, C-C bond formation, Carbon nucleophiles, Homogeneous catalysis, Palladium",

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T1 - Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst

AU - Patil, Nitin T.

AU - Kadota, Isao

AU - Shibuya, Akinori

AU - Young, Soo Gyoung

AU - Yamamoto, Yoshinori

PY - 2004/7

Y1 - 2004/7

N2 - We have developed an efficient and ecochemical process for the allylation of carbon pronucleophiles with alkynes. The reaction of alkynes with various active methynes and methylenes in the presence of Pd(PPh3) 4/acetic acid gave the corresponding allylated products in high yields and high regioselectivities. In the present catalytic system, the key is the use of carboxylic acid which dramatically enhances the rate of the reactions. One of the important features of this process is that neither a leaving group is liberated nor is a stoichiometric amount of base needed to generate the nucleophiles.

AB - We have developed an efficient and ecochemical process for the allylation of carbon pronucleophiles with alkynes. The reaction of alkynes with various active methynes and methylenes in the presence of Pd(PPh3) 4/acetic acid gave the corresponding allylated products in high yields and high regioselectivities. In the present catalytic system, the key is the use of carboxylic acid which dramatically enhances the rate of the reactions. One of the important features of this process is that neither a leaving group is liberated nor is a stoichiometric amount of base needed to generate the nucleophiles.

KW - Alkynes

KW - Allylation

KW - C-C bond formation

KW - Carbon nucleophiles

KW - Homogeneous catalysis

KW - Palladium

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Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst

Abstract

Keywords

ASJC Scopus subject areas

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