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We are running Exchange 2013 in a Hybrid Enviroment with Office 365 and we want to send all mails via Exchange Online. If we use the Outbound to Office 365 connector for all addresses (adding * at address space) we get the errormessage "451 4.4 0 primary target ip address responded with 454 4.7.5 Certificate validation failure."

What is the correct way to send all mails via Exchange Online or is that not possible?

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We've just recently moved to a Office 365 Hybrid setup, but we've been using EOP for quite a while. I mention it because you might need to check the connectors in the Office 365 EAC to make sure they're setup properly. Specifically take a look at the Inbound connector (from Your organization to Office 365). It's likely setup to verify your connection through a certificate. Make sure it's the same certificate you have installed on Exchange.

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Mentioned issue can occur because self signed certificate is used in Exchange 2013 server. check if you are using valid certificate.

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