A sequential direct arylation/Suzuki-Miyaura cross-coupling transformation of unprotected 2′-deoxyadenosine affords a novel class of fluorescent analoguesElectronic supplementary information (ESI) available: Experimental details (including characterisation data for all compounds) and X-ray data for 5d and 5i, including cif files. CCDC: 779419. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c0cc02043e

Novel rigid 8-biaryl-2′-deoxyadenosines with tuneable fluorescent properties can be accessed by an efficient sequential catalytic Pd 0 -coupling approach. Novel rigid 8-biaryl-2′-deoxyadenosines with tuneable fluorescent properties are formed efficiently by sequential direct arylation/Suzuki couplings.