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The [4+2] cycloaddition reaction of the (dimesitylphosphino)cyclopentadienes 5a,b with N-phenylmaleimide gave the norbornene derivative 9. Its reduction with LiAlH4 produced the N-phenylpyrrolidino-annulated system 10. Treatment with Piers’ borane gave the respective P/B FLP 12 as the major product, which cleaved dihydrogen under mild conditions to yield the phosphonium/hydrido borate product 14. Reaction of the phosphino-norbornene 10 with 2 M equiv. of Piers? borane [HB(C6F5)2] followed by exposure to dihydrogen eventually gave the HB(C6F5)2 adduct 15. This served as a catalyst for the hydrogenation of a series of chalcone derivatives. The system requires a pre-activation period before becoming active for the conjugated enone hydrogenation.
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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion