DisplayArticleForFree.cfm - 40TH ANNIVERSARY ARTICLE...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
Carbon–carbon bonding made easy Akira Suzuki DOI: 10.1039/b507375h The palladium-catalyzed cross-coupling reaction between organoboranes and organic electrophiles in the presence of base was first developed 30 years ago. It offers a powerful and general methodology for forming carbon–carbon bonds. The scope of the reaction has continued to evolve and broaden to meet modern synthetic requirements. Introduction Reactions in which new carbon–carbon bonds are formed are key steps in building the complex, bio-active mole- cules developed as drugs and agro- chemicals. They are also vital in developing the new generation of inge- niously-designed organic materials with novel electronic, optical or mechanical properties, likely to play a significant role in the burgeoning area of nanotechnology. During the past 40 years, the most important carbon–carbon bond-forming methodologies have involved using transi- tion metals to mediate the reactions in a controlled and selective manner. Perhaps themostwidely usedofthese chemistries is Suzuki coupling, which is the cross- coupling reaction of various organoboron compounds with organic electrophiles catalyzed by a palladium complex. It is now regarded as an integral part of any synthetic route used to build complex organic chemicals. Suzuki coupling has many advantages. The reactants are readily available, non- toxic, and air- and water-stable. They react under mild conditions and are amenable to a variety of reaction conditions, including the use of aqueous solvents and substrate supports. The inorganic boron byproduct can be easily removed after the reaction. Most impor- tant of all, the coupling proceeds with high regio- and stereoselectivity, and is little affected by steric hindrance. It does not affect other functional groups in the molecule, and can be used in one-pot strategies. The reaction has proved to be extremely versatile. It was first carried out between alkenyl reactants but over the years, we and others have extended its range to couple carbons in aryl, alkyl and alkynyl groups under a wide variety of conditions, as this review shows. A route to conjugated alkadienes In the mid-1970s, our group at Hokkaido University was attempting to find a way of synthesizing conjugated alkadienes stereo- and regio-selectively. Many such compounds have interesting biological activity – antibacterial, antiviral and so on – and so are of great importance in medicinal and biological chemistry. At that time, research into developing simple and general methods for creating the necessary carbon–carbon bonds between unsaturated species was still in its infancy. In the previous few years, several approaches had been developed utilizing metal-mediated cross-coupling reactions, 1 but although some were successful, their scope was limited by either the type of organometallic reagent or the procedure employed. Like many chemists, we believed that
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 02/17/2011 for the course CHEMISTRY 101 taught by Professor Csr during the Spring '11 term at University of Louisville.

Page1 / 5

DisplayArticleForFree.cfm - 40TH ANNIVERSARY ARTICLE...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online