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Abstract:
Highly selective heterogeneous Heck coupling has been demonstrated inside a series of metal–organic frameworks (MOFs). These MOFs, Zn4O(BDC-NH2)n(BDC)(3 − n) (n = 3, 2.4, 1.8, 1.2, 0.9, 0.75, 0.6, 0.3, and 0.15), have been synthesized with different amounts of 1,4-benzenedicarboxylate (BDC) and 2-amino-1,4-benzenedicarboxylate (BDC-NH2) incorporated into their structure. The BDC-NH2 is functionalized by covalent postmodification with salicylic aldehyde for binding catalytically active Pd(II) ions. The catalytic activity of the embedded Pd(II) ions was tested via heterogeneous Heck coupling to produce resveratrol trimethyl ether, a pharmaceutically relevant precursor. It is also found during catalytic testing that a trade-off exists between amount of metalation and pore blocking.
