Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
J Am Chem Soc. 2010 Aug 11;132(31):10686-8. doi: 10.1021/ja105161f.
The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of regioselection is consistent with a reaction that operates by a 3,3' reductive elimination reaction. In the presence of appropriate chiral ligands, this reaction is rendered enantioselective and applies to both aromatic and aliphatic allylic carbonates.
Pd 催化的烯丙基碳酸酯和烯丙基 B(pin)的交叉偶联反应被描述。该反应的区域选择性对配体的咬角敏感,小咬角配体有利于支链取代产物。这种区域选择性模式与通过 3,3'还原消除反应进行的反应一致。在适当的手性配体存在下,该反应可实现对映选择性,适用于芳香族和脂肪族烯丙基碳酸酯。