Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt3, the Mizoroki–Heck reaction of dienes delivers linear products under Ni(dppe)Cl2 catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF, the use of bulky ligand IPr diverts the selectivity from linear products to branched products. Highly aryl-substituted compounds can be transformed from dispersive Mizoroki–Heck products programmatically. Preliminary experimental studies are carried out to elucidate the role of additives.
Amides have played a vital role in polymeric materials, natural products and pharmaceuticals. In recent years, transition metal catalyzed C−N bond formation reaction provides a reliable strategy for amides construction. Herein, we disclosed a photo‐induced electrophilic amidation reaction with N‐methoxyamides and arylboronic acids at low temperature using a simple iron salt as the catalyst precursor. Initial mechanistic studies suggested that crucial amide radical species was involved.
The formation of one unavoidable byproduct in traditional disproportionation reactions limits their applications in synthesis. Inspired by convergent disproportionation, we develop an iodine-induced cyclization and oxidation of allylic alcohols to produce highly functionalized bicyclo[3.2.1]octanes through creation of six new bonds. Guided by the mechanism, we elaborated a variety of other bicyclo[3.2.1]octanes bearing distinct groups with presynthesized dienes and enones as the starting materials. This work provides a divergent access to bicyclo[3.2.1]octane frameworks.
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