Palladium‐catalyzed Atroposelective Interannular C−H Arylation of Biaryl Aldehydes with Aryl Iodides Enabled by a Transient Directing Group Strategy

Abstract

A concise synthesis of axially chiral biaryl aldehydes through Pd/amino acid-catalyzed atroposelective interannular CÀ H arylation of biaryl aldehydes with aryl iodides is developed. This reaction proceeds smoothly involving excellent enantiocontrol and accomplishes with good tolerance of functional groups. Moreover, the readily accessible scale-up synthesis and further transformation of products has highlighted the potential utility of this asymmetric catalytic protocol.

Crafting 1,4-diaryl spirobifluorene hosts in OLEDs via interannular C–H arylation: synergistic effects of molecular linearity and orthogonality

“…The current compromise solution to this issue relied on (i) incorporating blocking groups at both competitive reaction sites and (ii) utilizing an alkene insertion/b-oxygen elimination/protonolysis/dehydration cascade process with strained 7-oxabenzonorbornadienes as the arylation reagents. 32,33 However, the former cannot access 4aryl SBFs because blocking groups of biphenyl-2-formaldehyde substrates are difficult to remove. The latter only affords benzaldehydes containing binaphthyl units as the main product, which are unable to be transformed into the SBF structure.…”