Reaction of an (Alkyl)(alkenyl)(alkynyl)iridium(III)
Complex with HCl: Intramolecular C−C Bond Formation
from Alkyl, Alkenyl, and Alkynyl Groups Coordinated to
“Ir(CO)(PPh3)2”. H/D Exchange between CH3 and DCl
Posted on 1999-10-21 - 00:00
Reaction of the (alkyl)(alkenyl)(alkynyl)iridium(III) complex [Ir(CH3)(CHCHNEt3)(C⋮C(p-C6H4CH3))(CO)(PPh3)2]ClO4 (3) with aqueous HCl initiates an intramolecular coupling
reaction between −CH3 and −C⋮C(p-C6H4CH3) groups to give [Ir(C(CH3)CH(p-C6H4CH3)(CHCHNEt3)(Cl)(CO)(PPh3)2]ClO4 (5), which further reacts with aqueous HCl to produce
[Ir(CHCHNEt3)(Cl)2(CO)(PPh3)2]ClO4 (6) and cis-CH3CHCH(p-C6H4CH3) (7). Complex 5
yields the C−C coupling product [(p-C6H4CH3)HCC(CH3)CHCHNEt3]ClO4 (8) when it is
refluxed in CHCl3. The (alkyl)bis(alkynyl)iridium(III) compound Ir(CH3)(C⋮C(p-C6H4CH3))2(CO)(PPh3)2 (4) reacts with aqueous HCl to give H2CCCH(p-C6H4CH3) (9). Complex 3
reacts with excess DCl to give the d5 isotopomer CD3CDCD(p-C6H4CH3) (7-d5), while the
reaction of 4 with DCl gives the d1 isotopomer H2CCCD(p-C6H4CH3) (9-d1). Plausible
reaction pathways are discussed for the formation of 7 and 9 and for the H/D exchange to
give the isotopomer 7-d5.
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Chin, Chong Shik; Cho, Haeyeon; Won, Gyongshik; Oh, Moonhyun; Ok, Kang Min (2016). Reaction of an (Alkyl)(alkenyl)(alkynyl)iridium(III)
Complex with HCl: Intramolecular C−C Bond Formation
from Alkyl, Alkenyl, and Alkynyl Groups Coordinated to
“Ir(CO)(PPh3)2”. H/D Exchange between CH3 and DCl. ACS Publications. Collection. https://doi.org/10.1021/om9903442
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