Is it possible to generate(mine) a block with specific transaction via bitcoin-cli on regtest?
When you run generate, it mines a block with the transactions in the mempool:

generate nblocks ( maxtries )

Mine up to nblocks blocks immediately (before the RPC call returns) to an address in the wallet.


If you want those new coins to be mined to a specific address, you can use generatetoaddress

You can create transactions and submit them to the mempool either using the wallet RPC, e.g. sendtoaddress or using the rawtransactions RPC:
e.g. 


createrawtransaction
signrawtransaction
sendrawtransaction


sendrawtransaction will put the transaction in the mempool, which can then be included in the next block using generate