Single and Double Suzuki−Miyaura Couplings with Symmetric Dihalobenzenes
- 24 March 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (9), 3730-3733
- https://doi.org/10.1021/jo050105q
Abstract
m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.Keywords
This publication has 12 references indexed in Scilit:
- Practical Synthesis of Iodo Phenothiazines. A Facile Access to Electrophore Building BlocksThe Journal of Organic Chemistry, 2003
- A convenient synthesis of unsymmetrically substituted terphenyls of biologically active stilbenes via a double Suzuki cross-coupling protocolTetrahedron Letters, 2003
- Convenient synthesis of functionalized terphenylsTetrahedron Letters, 2003
- Cross-coupling reactions via organoboranesJournal of Organometallic Chemistry, 2002
- Palladium-catalyzed cross-coupling reaction of bis(ferrocenyl)mercury with aryl iodidesTetrahedron Letters, 2000
- Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998Journal of Organometallic Chemistry, 1999
- Synthesis of biaryls via the cross-coupling reaction of arylboronic acidsPublished by Elsevier ,1998
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Directed ortho metalation - suzuki cross coupling connections. Convenient regiospecific routes to functionalized m- and p-teraryls and m-quinquearylsTetrahedron Letters, 1992
- Dramatic rate enhancement of Suzuki diene synthesis. Its application to palytoxin synthesisJournal of the American Chemical Society, 1987