This disclosure relates to new synthetic methods for preparing substituted fluorene compounds and fluorenyl-substituted metallocenes, which are useful in applications such as olefin polymerization catalysis. The new methods involve a Pd-catalyzed, one-pot tandem reaction of a 1,2-dihalobenzene with a 2-methylarylboronic acid using non-conventional and unexpected reaction conditions, which may improve existing methods by providing higher yields, higher selectivity, and/or the ability to incorporate a wider range of substituents with various steric and electronic properties and regiochemistries which are difficult to access using existing methods.