120265-05-6Relevant articles and documents
Regiocontrolled synthesis and optical resolution of mono-, di-, and trisubstituted tribenzotriquinacene derivatives: Key building blocks for further assembly into molecular squares and cubes
Xu, Wen-Rong,Chow, Hak-Fun,Cao, Xiao-Ping,Kuck, Dietmar
, p. 9335 - 9346 (2014)
The regiocontrolled syntheses of four chiral C1- or C3-symmetrical tribenzotriquinacene (TBTQ) derivatives bearing methoxy or hydroxy groups at the peripheral positions [(2,6-(OMe)2, (±)-18 and (±)-20; 2,6-(OH)2
The Halogen–Samarium Exchange Reaction: Synthetic Applications and Kinetics
Anthore-Dalion, Lucile,Benischke, Andreas D.,Wei, Baosheng,Berionni, Guillaume,Knochel, Paul
supporting information, p. 4046 - 4050 (2019/02/26)
Fast I/Sm and Br/Sm exchanges take place when various aromatic or heterocyclic iodides and bromides are treated with nBu2SmCl?4 LiCl and nBu3Sm?5 LiCl, respectively. The resulting organosamarium reagents were efficiently quenched with aldehydes, ketones, and imines. Also, they undergo acylations when treated with N,N-dimethylamides leading to ketones. The rate of the Br/Sm exchange for a typical aryl bromide was determined and found to be 8.5×105 faster than the Br/Mg exchange, indicating that the rate of a metal-exchange is related to the ionic character of the carbon–metal bond and to the metal electronegativity.
Synthesis of Polyfunctionalized Triaryllanthanum Reagents by Using Ph3La and Related Species as Exchange Reagents
Benischke, Andreas D.,Anthore-Dalion, Lucile,Kohl, Fabien,Knochel, Paul
supporting information, p. 11103 - 11109 (2018/08/09)
Ph3La?5 LiCl and the related (m-xylyl)3La?5 LiCl were used as Hal/La exchange reagents (Hal=Br, I) for the preparation of various triaryl- and triheteroaryl-lanthanum derivatives. These new exchange reagents are compatible with isoquinolines and some functional groups such as a nitrile or an ester. The reactivity of the resulting lanthanum compounds towards electrophiles, such as ketones, aldehydes, N,N-dimethylamides, and primary alkyl halides was investigated. Additionally, a Pd-catalyzed cross-coupling procedure with aryl bromides was developed.