Non‐Bonding Interactions Enable the Selective Formation of Branched Products in Palladium‐Catalyzed Allylic Substitution Reactions. Issue 17 (4th July 2018)

• Record Type: Journal Article
• Authors: Wang, Ya‐Ni; Lu, Liang‐Qiu; Xiao, Wen‐Jing
• Is Part Of: Chemistry, an Asian journal. Volume 13:Issue 17(2018)
• Page Start: 2174
• Page End: 2183
• Publication Date: 2018-07-04
• Subjects: allylic substitution -- branched products -- noncovalent interactions -- palladium -- regioselectivity; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201800496
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: Palladium‐catalyzed allylic substitution reactions have become established as an important tool for the construction of carbon−carbon and carbon−heteroatom bonds in modern organic synthesis. However, controlling the regioselectivity of this type of transformation to afford chiral branched products, in addition to controlling the enantioselectivity, is a significant challenge. Excitingly, controlling nonbonding interactions between the substituents on the π‐allyl−palladium intermediate and the nucleophile or palladium catalyst has been shown to be effective in achieving this goal. This Focus Review highlights representative advances in this field, according to the mode of non‐bonding interaction, including hydrogen‐bonding, electrostatic, and coordination interactions. Abstract : Branch Manager : A wide range of palladium‐catalyzed allylic substitution reactions with high selectivities for the branched products have been developed by utilizing non‐bonding interactions. This Focus Review highlights these advances and explains how such interactions can be used to switch the regioselectivity from linear to branched products.