Concepedia

Use of Thallium(I) Ethoxide in Suzuki Cross Coupling Reactions

Scott A. Frank, Hou Chen, Roxanne K. Kunz, Matthew Schnaderbeck, William Roush

Organic Letters · 2000 · 127 citations · 16 references

DOI

Concepts

Abstract

[reaction: see text]Thallium(I) ethoxide promotes Suzuki cross couplings for a range of vinyl- and arylboronic acids with vinyl and aryl halide partners in good to excellent yields. This reagent offers distinct advantages over thallium(I) hydroxide in terms of commercial availability, stability, and ease of use.

References

16

Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998

Akira Suzuki · Journal of Organometallic Chemistry · 1999 · 2.9K citations

, , +12

A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides

Norio Miyaura, Kinji Yamada, Akira Suzuki · Tetrahedron Letters · 1979 · 2.2K citations · Full text

, , +12

Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes

Norio Miyaura, Kinji Yamada, Hiroshi Suginome et al. · Journal of the American Chemical Society · 1985 · 514 citations

, , +9

Dramatic rate enhancement of Suzuki diene synthesis. Its application to palytoxin synthesis

Jun’ichi Uenishi, Jean Marie Beau, Robert W. Armstrong et al. · Journal of the American Chemical Society · 1987 · 303 citations

, , +6

Cross-Coupling Reaction of Alkyl- or Arylboronic Acid Esters with Organic Halides Induced by Thallium(I) Salts and Palladium-Catalyst

Makoto Sato, Norio Miyaura, Akira Suzuki · Chemistry Letters · 1989 · 166 citations

, , +16