Synthesis of the First Stable Palladium Allenylidene Complexes | Zendy

Florian Kessler | Zendy; Normen Szesni | Zendy; Kaija PõhakoEsko | Zendy; B. Weibert | Zendy; Helmut Fischer | Zendy

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Synthesis of the First Stable Palladium Allenylidene Complexes

Author(s) -

Florian Kessler,

Normen Szesni,

Kaija PõhakoEsko,

B. Weibert,

Helmut Fischer

Publication year - 2008

Publication title -

organometallics

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.231

H-Index - 172

eISSN - 1520-6041

pISSN - 0276-7333

DOI - 10.1021/om800843e

Subject(s) - chemistry , cationic polymerization , palladium , yield (engineering) , medicinal chemistry , oxidative addition , stereochemistry , catalysis , organic chemistry , metallurgy , materials science

Oxidative addition of BrC≡CC(═O)NR2 to [Pd(PPh3)4] affords the trans-alkynylbromopalladium complexes trans-[Br(PPh3)2Pd−C≡CC(═O)NR2] (NR2 = NMe2 (2a), N(CH2)4) (2b)). Subsequent reaction of 2a,b with PiPr3 in excess gives trans-[Br(PiPr3)2Pd−C≡CC(═O)NR2] (5a,b). The analogous reaction of 2b with P(C6H4OMe-4)3 gives trans-[Br(P{C6H4OMe-4}3)2Pd−C≡CC(═O)NR2] (7b), and that of 2a with trifluoroacetate gives trans-[(F3CCOO)(PPh3)2Pd−C≡CC(═O)NMe2] (9a). Methylation of 2a,b, 7b, and 9a with either MeOTf or [Me3O]BF4 and ethylation of 2a,b with [Et3O]BF4 yield the first cationic allenylidene complexes of palladium, trans-[R*(PR′3)2Pd−C≡CC(OMe)NR2]+X− (R* = Br, CF3COO; R′ = Ph, C6H4OMe-4, iPr; X = OTf, BF4).

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