Equilibration of the oxidative addition product of tetrakis(triphenylphosphine) palladium and electron-rich aryl halides leads to product scrambling in the Stille reaction

Journal Article · Fri Jan 13 04:00:00 EST 1995 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo00106a006· OSTI ID:379223

Segelstein, B E; Butler, T W; Chenard, B L ^[1]

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1. Pfizer Inc., Groton, CT (United States)

The authors report here that the initially formed intermediate in the Stille reaction (oxidative addition of Pd{sup 0} into the aryl halide) may undergo aryl-phenyl exchange with the triphenylphosphine ligand yielding a mixture of biaryl products which may be difficult to separate. In addition, the authors find that the Stille catalytic cycle may be entered independently via oxidative addition of palladium into the tetraphenylphosphonium ion. These observations suggest that an equilibrium may exist between tetraarylphosphonium ion and the initially formed Pd{sup 2+} intermediate. 1 tab.

• Sponsoring Organization: USDOE
• OSTI ID: 379223
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 1 Vol. 60; ISSN 0022-3263; ISSN JOCEAH
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
CATALYSIS
CATALYTIC EFFECTS
EQUILIBRIUM
OXIDATION
PALLADIUM COMPLEXES
REACTION INTERMEDIATES