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A sustainable C(sp2)–C(sp3) cross-electrophile coupling was developed between readily available 5-bromophthalide and 1-benzyl-4-iodopiperidine under micellar conditions, leading to a key intermediate of one of our development compounds. Copper was found to play a crucial role as a co-catalyst in this dual catalysis system. The chemistry and process were successfully demonstrated in a kilo scale to deliver sufficient drug substance to the clinical campaigns. This is the first reported scale-up of such a challenging cross-electrophilic coupling that uses an aqueous medium, and not undesirable reprotoxic polar aprotic solvents (e.g. DMF, DMAc, and NMP). [ABSTRACT FROM AUTHOR]

The site selective C(sp2)–H bond functionalization of olefins has been achieved through a visible-light-induced photoredox-quinuclidine dual catalysis upon merging the quinuclidinium radical cation addition to alkene strategy and the distal heteroaryl ipso-migration strategy. This synthetic protocol features a simple operation with readily available starting materials in good step-economy to access alkenylheteroaromatic products in moderate to good yields under mild conditions. A plausible cascade catalytic reaction mechanism is also proposed. [ABSTRACT FROM AUTHOR]

Carbon dioxide as a classic C1 source has long been investigated in organic synthetic chemistry. Diverse catalytic methods for CO2 activation have been reported over the past several decades. In this minireview, we mainly focus on detailing recent advances (since 2020) in utilizing carbon dioxide to attain the carboxylation of organic motifs via photoredox and metallaphotoredox catalysis. [ABSTRACT FROM AUTHOR]

A gold-catalyzed method for the construction of indolizines with eight-membered rings has been developed. The reaction proceeded through a two-fold hydroarylation with indole or pyrrole derivatives containing a 1,6-diyne using a tri(1-adamantyl)phosphine gold complex as the catalyst, affording 1,8-disubstituted indolizines in moderate to good yields in DCE at 80 °C. The potential usefulness of these indolizines as blue or green OLEDs has been also disclosed. [ABSTRACT FROM AUTHOR]

Enantioselective Pd(ii)-catalyzed construction of [3.3.1]-bicyclic ketals from 2-hydroxyphenylboronic acid 1 and enone 3 is reported, yielding enantioenriched [3.3.1]-bicyclic ketals in up to 97% yields and 98% ee. [ABSTRACT FROM AUTHOR]