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A convenient method is developed to synthesize 1,1-diboronates from the corresponding N-tosylhydrazones. This method is also applicable to synthesize 1-silyl-1-boron compounds. Meanwhile, derivatization and consecutive Pd-catalyzed cross-coupling reactions with 1,1-boronates were explored, demonstrating the synthetic potential of 1,1-diboronates.
An efficient and mild synthesis of 9H-fluorene derivatives through a Pd(0)-catalyzed cross-coupling reaction of 1,1-diboronates with 2,2'-dibromobiphenyls has been developed. This reaction features high yields, operational simplicity, and mild reaction conditions, thus providing an excellent alternative to published methods for 9H-fluorene synthesis.
Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.