470663-71-9

Upstream product

• 1333-74-0 hydrogen 

Downstream Products

• 956795-00-9 acetonitrile(hydrido)(2-phenylpyridinato)bis(triphenylphosphine)iridium(III) triflate 
• 470663-73-1 Ir(CHCH₂)2(CH₃CN)2(P(C₆H₅)3)2⁽¹⁺⁾*CF₃SO₃^(1-)=Ir(CHCH₂)2(CH₃CN)2(P(C₆H₅)3)2CF₃SO₃ 

Relevant academic research and scientific papers

Carbon-carbon bond formation between adjacent alkenyl ligands: η3-allyl iridium(III) and η4-butadiene iridium(I) complexes from a cis-bis(alkenyl) iridium(III) complex

A carbon-carbon bond is formed between the α-carbons of the alkenyl ligands of the cis-bis(ethenyl)iridium complex [Ir(-CH=CH2)2(CH3CN)2 (PPh3)2]+ (2) to produce the η3-allyl complex [Ir(η3-CH3 CHCHCH2)(NCCH3)2 (PPh3)2]2+ (4) in the reaction of 2 with H+, and η4-butadiene complexes Ir(η4-CH2=CHCH=CH2)(A) (PPh3)2 (A = -CH=CH-+NEt3 (6), -C≡ CR (7)) in reactions of 2 with terminal alkynes (RC≡CH; R = H, Ph, and p-C6H4CH3) in the presence of NEt3. The deuterium labeling experiments suggest an initial attack of H+ on the β-carbon of an ethenyl ligand to lead to the C-C bond formation between the α-carbons of the two alkenyl groups of 2 to produce 4.

Synthesis of cross-conjugated olefins from alkynes: Regioselective C-C bond formation between alkynes

Reactions of cis-dihydrido complex [Ir(H)2(NCCH3)2(PPh3)2] + (1) with HC≡CH and RC≡CH (R = C6H5, p-C6H4CH3, cyclohex-1-enyl, C(CH3)=CH2, C(CH3)3) produce cross-conjugated hexatrienes (RCH=C(CH=CH2)2, R-HEX) and octatetraenes (H2C=CH-CR=CH-C(-CH= CH2)=CHR, R2-OCT). Two molecules of HC≡CH are inserted into Ir-H bonds of 1 to give cis-bis(ethenyl) complex [Ir(CH==CH2)2(NCCH3)2(PPh3 )2]+ (2), which reacts with RC≡CD to produce both R-HEX-d1 (RCD=C(CH=CH2)2) and R2-OCT-d2 (H2C=CH-CR=CD-C(-CH= CH2)=CDR). R-HEX are exclusively obtained from the reactions of RC≡CH with [Ir(CH= CH2)2(CO)2(PPh3)2]+ (3). Alkynyl cis-bis(ethenyl) complexes Ir(CH=CH2)2(C≡CR)(CO)(PPh3)2 (4, R = C6H5 (a), p-C6H4CH3 (b), cyclohex-1-enyl (c)) react with D+ to give η4-R-HEX-d1 complexes [Ir(η4-RCD=C(CH=CH2)2)(CO)(PPh3) 2]+ (5-d1) from which R-HEX-d1 are obtained in the presence of a base. Di- and trinuclear alkynyl-bis(alkenyl) complexes [L5Ir-C≡Cp-C6H4-C≡C-IrL5 ] (7, L5 = (-CH=CH2)2(CO)(PPh3)2) and [L5Ir-C≡C-m,m-C6H3-(C≡C-IrL5 )2] (8, L5 = (-CH=CH2)2(CO)(PPh3)2) react with H+ to produce extended cross-conjugated olefins, p-C6H4-(HEX)2 and m,m-C6H3-(HEX)3, respectively, in high yields. Plausible reaction pathways involve alkenyl-vinylidene complexes that undergo the C-C bond formation reaction between the two hydrocarbyl ligands to produce the cross-conjugated olefins.