97443-80-6Relevant articles and documents
An Alternative Synthesis of Cycloalkyl-Substituted CPA Catalysts and Application in Asymmetric Protonation Reactions**
McLean, Liam A.,Watson, Allan J. B.
, p. 4943 - 4945 (2021/09/28)
An alternative synthesis of cycloalkyl-substituted CPA catalysts is reported. A Negishi coupling offers improved yields and purity of the necessary 1,3,5-tri(cycloalkyl)benzenes. Limitations in the use of commercial organozinc reagents have been identifie
Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations
Romanov-Michailidis, Fedor,Romanova-Michaelides, Maria,Pupier, Marion,Alexakis, Alexandre
supporting information, p. 5561 - 5583 (2015/03/30)
The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.
A new biarylphosphine ligand for the Pd-catalyzed synthesis of diaryl ethers under mild conditions
Salvi, Luca,Davis, Nicole R.,Ali, Siraj Z.,Buchwald, Stephen L.
, p. 170 - 173 (2012/03/08)
A new bulky biarylphosphine ligand (L8) has been developed that allows the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols under milder conditions than previously possible. A direct correlation between the size of the ligand substituents in the 2′, 4′, and 6′ positions of the nonphosphine containing ring and the reactivity of the derived catalyst system was observed. Specifically, the rate of coupling increased with the size of these substituents.