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 journalArticle

44 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 languageEnglish
Pages (from-to)800-804
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number7
DOIs
Publication statusPublished - Jul 2004
Externally publishedYes

Fingerprint

Allylation
Regioselectivity
Nucleophiles
Alkynes
Palladium
Carboxylic acids
Acetic acid
Acetic Acid
Carbon
Catalysts
Carboxylic Acids

Keywords

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

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

Cite this

Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst. / Patil, Nitin T.; Kadota, Isao; Shibuya, Akinori; Young, Soo Gyoung; Yamamoto, Yoshinori.

In: Advanced Synthesis and Catalysis, Vol. 346, No. 7, 07.2004, p. 800-804.

Research output: Contribution to journalArticle

Patil, Nitin T. ; Kadota, Isao ; Shibuya, Akinori ; Young, Soo Gyoung ; Yamamoto, Yoshinori. / Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst. In: Advanced Synthesis and Catalysis. 2004 ; Vol. 346, No. 7. pp. 800-804.
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