A significant limitation of practical quantum key distribution (QKD) setups is currently their limited operational range. It has recently been emphasized (X. Ma, C.-H. F. Fung, and H.-K. Lo., Phys. Rev. A, 76:012307, 2007) that entanglement-based QKD systems can tolerate higher channel losses than systems based on weak coherent laser pulses (WCP), in particular when the source is located symmetrically between the two communicating parties, Alice and Bob. In the work presented here, we experimentally study this important advantage by implementing different entanglement-based QKD setups on a 144~km free-space link between the two Canary Islands of La Palma and Tenerife. We established three different configurations where the entangled photon source was placed at Alices location, asymmetrically between Alice and Bob and symmetrically in the middle between Alice and Bob, respectively. The resulting quantum channel attenuations of 35~dB, 58~dB and 71~dB, respectively, significantly exceed the limit for WCP systems. This confirms that QKD over distances of 300~km and even more is feasible with entangled state sources placed in the middle between Alice and Bob.
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