Angewandte Chemie - International Edition p. 3620 - 3624 (2016)
Update date:2022-08-04
Topics:
Buter, Jeffrey
Heijnen, Dorus
Vila, Carlos
Hornillos, Valentín
Otten, Edwin
Giannerini, Massimo
Minnaard, Adriaan J.
Feringa, Ben L.
A palladium-catalyzed direct synthesis of symmetric biaryl compounds from aryl halides in the presence of tBuLi is described. In situ lithium-halogen exchange generates the corresponding aryl lithium reagent, which undergoes a homocoupling reaction with a second molecule of the aryl halide in the presence of the palladium catalyst (1 mol %). The reaction takes place at room temperature, is fast (1 h), and affords the corresponding biaryl compounds in good to excellent yields. The application of the method is demonstrated in an efficient asymmetric total synthesis of mastigophorene A. The chiral biaryl axis is constructed with an atropselectivity of 9:1 owing to catalyst-induced remote point-to-axial chirality transfer. It takes two: A palladium-catalyzed direct homocoupling of aryl halides in the presence of tBuLi enabled the synthesis of even tetra-ortho-substituted symmetric biaryl compounds in high yield (see scheme). The method was applied to the asymmetric synthesis of mastigophorene A in just eight steps through straightforward enantioselective installation of the benzylic quaternary stereocenter and highly diastereoselective homocoupling.
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