Direct prenylation of aromatic and alpha,beta-unsaturated carboxamides via iridium-catalyzed C-H oxidative addition-allene insertion.
Exposure of aromatic carboxamides 1e-1m, heteroaromatic carboxamides 1n-1p, and alpha,beta-unsaturated carboxamides 1q-1s to 1,1-dimethylallene in the presence of the a cationic iridium complex derived from [Ir(cod)(2)]BAr(F)(4) and rac-BINAP results in direct C-H prenylation to furnish adducts 2e-2m, 2n-2p, and 2q-2s, respectively, in good isolated yields as single isomers.
Zhang
Yong Jian
YJ
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Skucas
Eduardas
E
Krische
Michael J
MJ
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D054876:Prenylation; D013237:Stereoisomerism
D000466:Alkadienes; D006841:Hydrocarbons, Aromatic; D016877:Oxidants; D007495:Iridium; C025947:propadiene