By Yaushi Nishihara (auth.), Yasushi Nishihara (eds.)
“Applied Cross-Coupling Reactions” offers scholars and lecturers of complicated natural chemistry with an summary of the historical past, mechanisms and functions of cross-coupling reactions. because the discovery of the transition-metal-catalyzed cross-coupling reactions in 1972, a number of artificial makes use of and commercial purposes were constructed. The mechanistic reviews of the cross-coupling reactions have disclosed that 3 basic reactions: oxidative addition, transmetalation, and reductive removing, are desirous about a catalytic cycle. Cross-coupling reactions have allowed us to supply a number of compounds for business reasons, corresponding to common items, prescription drugs, liquid crystals and conjugate polymers to be used in digital units. certainly, the Nobel Prize for Chemistry in 2010 used to be provided for paintings on cross-coupling reactions. during this e-book, the new traits in cross-coupling reactions also are brought from the viewpoint of synthesis layout and catalytic actions of transition-metal catalysts.
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Extra resources for Applied Cross-Coupling Reactions
Okuda and Y. 5 Migita–Kosugi–Stille Coupling Although some cross-couplings might not be useful for highly reactive substrates bearing functional groups such as epoxides which are sensitive to both acids and bases, the mild and neutral Migita–Kosugi–Stille coupling has often been used in the key steps of the natural product syntheses. This section introduces representative examples of how Migita–Kosugi–Stille coupling can be used in natural product synthesis. 1 Synthetic Methods of Organotin Compounds When Migita–Kosugi–Stille is employed as a coupling reaction, synthesis of organotin compounds is required.
Bull Chem Soc Jpn 75:1333–1345 28. Kang S-K, Lee H-W, Jang S-B, Ho P-S (1996) Palladium-catalyzed cross-coupling of organoboron compounds with iodonium salts and iodanes. J Org Chem 61:4720–4724 2 Mechanisms and Fundamental Reactions 37 29. Dares S, Jeffery T, Genêt J-P, Brayer J-L, Demoute J-P (1996) Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium. Tetrahedron Lett 37:3857–3860 30. Sengupta S, Bhattacharyya S (1997) Palladium-catalyzed cross-coupling of arenediazonium salts with arylboronic acids.
One is the addition– elimination mechanism (path a) and the other is via the palladium carbene complex (path b). In both mechanisms, the reaction starts from a regioselective addition of the arylpalladium complex to the double bond of the a-substituted alkenylstannane. 10, first carbopalladation occurs to the alkenylstannane regioselectively to generate intermediate 5. The carbon–carbon bond in 5 rotates to give the syn configuration, from which b-hydrogen elimination takes place. The hydridopalladium complex adds to the generated alkenylstannane at the opposite position to give intermediate 6.