Here we have the oft-overlooked military plan Operation Pike, whose goal was to destroy the Soviet oil industry.
After the division of Poland and the signing of the Molotov-Ribbentrop Pact, the UK and France began looking for a way to destroy or at least weaken the USSR's economy. Noticing Germany's reliance on Soviet oil imports, they began looking into the possibility of hitting the oil refineries of the Caucasus, particularly Baku, where 90% of oil extraction and 80% of refinement took place. The goal would be crippling two countries for the price of one.
Serious planning began after the Winter War, with aerial reconnaissance and the movement of bombers to the Middle east. The French were more gung-ho about the operation, but the British were a lot more cautious. There were fears that the bombing run might lead to a German-Russian alliance against Western europe. Unfortunately, after Nazi Germany invaded France, the plans were discovered. However, after Operation Barbarossa, the plan was revived as a possibility to deny the Nazis access to oil fields.
But either way, with around 100 bombers only capable of carrying half a ton of bombs each, low payload and poor accuracy, it was extremely unlikely that they would've had a huge success on bombing the oil facilities. Not to mention, if the plan had actually succeeded and were carried out during Barbarossa, Russia would have suffered far more of the impact and it actually may have weakened the country at a time when a massive bulwark was
desperately needed. Whether or not that would actually be the catalyst for a Nazi victory is open to debate.