Copper mediated formation of carbon-heteroatom bonds using organoboron reagents and ultrasound

Bryan J. Musolino, George Kabalka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%.1 Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.

Original languageEnglish (US)
Pages (from-to)271-297
Number of pages27
JournalHeterocycles
Volume90
Issue number1
DOIs
StatePublished - Jan 1 2015

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Aniline Compounds
Indoles
Phenols
Sulfhydryl Compounds
Copper
Acetates
Carbon
Ultrasonics
Irradiation
Research

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Copper mediated formation of carbon-heteroatom bonds using organoboron reagents and ultrasound. / Musolino, Bryan J.; Kabalka, George.

In: Heterocycles, Vol. 90, No. 1, 01.01.2015, p. 271-297.

Research output: Contribution to journalArticle

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