Last minute winner
Libertad's Josiel made it 1-0 for Parana after 49 minutes by tapping in from close range after Horacio Gonzalez, Libertad's goalkeeper, was forced to parry a fierce strike from Dinelson.
Parana had to defend after Libertad stepped up the pressure to get an equaliser.
Roberto Gamarra shot over the crossbar and Martinez fired a shot from close range that Flavio tapped wide for a corner kick.
Libertad substitute Vladimir Marin fired a free kick into the right corner to level the score after 69 minutes, before Barone headed the winner from a corner kick a minute from time.
Juan Manuel Martinez scored three goals at Bogota, Colombia as Cucuta Deportivo cruised past Toluca in their first leg match to virtually guarantee a place in the quarter finals on their first tournament appearance.
|Toluca's joy was short lived as their early |
goal was eclipsed by Cucuta [EPA]
A defensive error allowed Toluca's Vicente Sanchez to score after only 25 seconds of play and he almost scored again after five minutes.
But Cucuta's Martinez scored from a powerful long-distance shot after 31 minutes, the first of his three goals which came in the remainder of the first half.
Charles Castro slid the ball through the legs of goalkeeper Hernan Cristante for Cucuta's second on 34 minutes.
Cucuta's final goal came with a minute from full-time, when Alex del Castillo scored off a pass from Blas Perez.
The two teams will meet again on Tuesday in Toluca, with winner advancing set to meet Uruguay's Nacional or Mexico's Necaxa.
At Montevideo, Nacional defender Diego Godin scored a goal for both sides on the way to eventually defeating Necaxa.
Nacional took the lead after seven minutes through Diego Vera but Necaxa levelled the score three minutes later with a goal from Kleber Boas.
Godin slotted the ball under Nexaca goalkeeper Federico Vilar through the first half to make it 2-1, but scored an own goal eight minutes into the second half.
Jorge Martinez put Nacional ahead for good after 52 minutes to set up a tight contest in the second leg.