3-Indolylphosphines as ligand for palladium in Suzuki–Miyaura coupling reaction of chloroarenes: substituent effects

Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles

“…Indole-based phosphine ligands such as CMphos, amide CMPhos in combination with a palladium metal precursor have been found to be effective catalysts for Suzuki–Miyaura coupling of unactivated aryl chlorides 17 and Buchwald–Hartwig amination. 18 To show the utility of this method for generating useful building blocks, a number of further transformations were carried out on products obtained in the course of these studies (Scheme 7).…”

“…Chromatography (petroleum ether/ethyl acetate = 50/1) afforded 8 (606.79 mg) in 63% yield as a white solid. 17…”

Preparation of phosphines through C–P bond formation

“…The reaction of an organometallic reagent with the P - atom of halophosphines is a classical method used for the synthesis of both alkenyl- and arylphosphines. The organometallic reagents are mostly Grignard reagents [ 136 – 138 ] or organolithium [ 139 – 142 ] derivatives. Other organometallic reagents such as aluminum [ 143 ] or organomercury [ 26 , 144 ] reagents have been used less frequently.…”

When cross-coupling partners meet indolylphosphines

“…Sarkar [29] cataCXium PIntB (L7a) [31, 36-37, 70, 72, 83] cataCXium PInCy (L7b) Buchwald-Hartwig amination,…”

“…Later, the same group developed an interesting ligand L6a for C-C bond coupling reaction (Table 4, entry 16) [29]. Study towards the ligand substituent effects towards the efficacy of this reaction was carried out.…”