2010
DOI: 10.1039/c0dt00086h
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Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine

Abstract: The hydrido complexes trans-[Pd(H)(4-C(5)NF(4))(PiPr(3))(2)] (3) and trans-[Pd(H)(4-C(5)NF(4))(PCy(3))(2)] (5) can be prepared by reaction of trans-[Pd(F)(4-C(5)NF(4))(PiPr(3))(2)] (2) or trans-[Pd(F)(4-C(5)NF(4))(PCy(3))(2)] (4) with HBpin (HBpin = 4,4,5,5-tetramethyl-1,3,2-dioxaborolane, pinacolborane). The iodo and triflato complexes trans-[Pd(I)(4-C(5)NF(4))(PiPr(3))(2)] (7) and trans-[Pd(OTf)(4-C(5)NF(4))(PiPr(3))(2)] (9) are generated on treatment of complex 3 with MeI or ethyltrifluoromethanesulfonate (… Show more

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Cited by 55 publications
(15 citation statements)
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“…. 259 These stoichiometric experiments support that the catalytic hydrodefluorination reaction occurs in the same way.…”
Section: Hydrodefluorination Reactionssupporting
confidence: 61%
“…. 259 These stoichiometric experiments support that the catalytic hydrodefluorination reaction occurs in the same way.…”
Section: Hydrodefluorination Reactionssupporting
confidence: 61%
“…The reaction scope was investigated and a range of fluoroarenes and heteroarenes were amenable to C−H zincation forming 2 a – t (Table 1 and Table 2). High chemoselectivity was observed despite the fact that [Pd(PCy 3 ) 2 ] is known to catalyse the functionalisation of C−F bonds of fluoroarenes [22, 23] . For fluoroarenes, the regiochemistry appears to be dictated by the ortho ‐fluorine effect, with substitution occurring at sites adjacent to at least one fluorine substituent.…”
Section: Resultsmentioning
confidence: 99%
“…The nickel fluoro complexes which have been synthesized can be considered as essential intermediates of a putative catalytic cycle. Note that it has been shown before that fluoro complexes often exhibit a higher reactivity than their chloro or bromo counterparts [18,19,[21][22][23][24][25][26][27][28][29]31,51,69]. Representative results of the cross coupling reactions of pentafluoropyridine Scheme 4.…”
Section: Bondmentioning
confidence: 96%