We tested this config in GNS3 (except the LAN interface) but R1 loopback0 was advertised normally on R2 and R2 could reach this loopback0.
Note: Although the configured loopback address is 4.4.4.4/24 but by default OSPF will advertise this route to loopback0 as 4.4.4.4/32 (most specific route to that loopback). In order to override this, we have to change the network type to point-to-point. After this OSPF will advertise the address to loopback as 4.4.4.0/24.