As shown in Scheme 1, two readily accessible building blocks, the 2,9-dibromo-phenanthrene 1 12 carrying two vinyl ether groups and two solubilizing n-butoxy substituents, and the 1,8-anthracene derivative 2 with two pinacol borate (Bpin) units, were subjected to Suzuki coupling reaction involving Pd2(dba)3, [( t Bu)3PH]BF4 and NaHCO3 in THF/H2O at 80 o C. MALDI-TOF mass spectrometry analysis indicates the formation of a series of oligomers ( ) with the terminal Bpin groups replaced by hydrogen atoms after 3 days. The crude product was extracted by dichloromethane (DCM), washed with water, and passed through a silica gel column. Without further purification, the mixture of the oligomer precursors 3 was subjected to Bi(OTf)3-mediated cyclization reaction in 1,2-dichloroethane (DCE) at 60 o C for 8 hours, and the fully fused expanded helicenes H1-H4 were isolated by preparative GPC in 33.3%, 13.5%, 4.1%, and 0.8% yield, respectively, over two steps. Their structures were unambiguously confirmed by X-ray crystallographic analysis (see below), NMR, and high-resolution mass spectrometry (see supporting information (SI)). The high regioselective cyclization could be due to the larger strain if the cyclization goes to the meso-carbon of the anthracene unit (formation of seven-membered ring) as compared to the β-carbons (formation of six-membered ring).