503274-64-4Relevant academic research and scientific papers
Phosphaadamantanes as ligands for palladium catalyzed cross-coupling chemistry: Library synthesis, characterization, and screening in the Suzuki coupling of alkyl halides and tosylates containing β-hydrogens with boronic acids and alkylboranes
Brenstrum, Tim,Gerristma, David A.,Adjabeng, George M.,Frampton, Christopher S.,Britten, James,Robertson, Alan J.,McNulty, James,Capretta, Alfredo
, p. 7635 - 7639 (2004)
A 15-member library of phosphaadamantane ligands has been prepared via P-arylation of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane. Screening of this tertiary phosphine collection has allowed for the rapid determination of the most suitable ligand, specifically 1,3,5,7-tetramethyl-6-(2,4- dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane, for facilitating Suzuki-type couplings of alkyl halides or tosylates containing β-hydrogens with either boronic acids or alkylboranes.
Single isomer trisubstituted olefins bearing alkyl groups
Rajagopal, Thivisha,Flynn, Alison B.,Ogilvie, William W.
experimental part, p. 8739 - 8744 (2011/01/04)
E-β-Chloro-α-iodo-α,β-unsaturated esters were converted to single isomer trisubstituted olefins bearing alkyl substituents by using and alkyl-Suzuki cross coupling. The process was highly selective, and the products in all cases were isolated as single isomers. Mechanistic investigations indicated that this process transfers a hydrogen from water to the α-position of the substrate, and then an alkyl group is introduced to the β-position of the intermediate template while replacing a chloride.
A method for palladium-catalyzed cross-couplings of simple alkyl chlorides: Suzuki reactions catalyzed by [Pd2(dba)3]/PCy3
Kirchhoff, Jan H.,Dai, Chaoyang,Fu, Gregory C.
, p. 1945 - 1947 (2007/10/03)
The window of reactivity is relatively narrow in the first Suzuki cross-coupling of alkyl chlorides with alkyl 9-borabicyclo[3.3.1]nonane (9-BBN) derivatives catalyzed by [Pd2(dba)3] [Eq. (1); dba = (E,E)-dibenzylideneacetone]: whereas good yields are obtained with the ligand tricyclohexylphosphane for ligands that are appreciably larger or smaller, essentially no coupling is observed. As the conditions are compatible with a variety of functional groups, this method introduces a new class of substrates into the family of potential partners in palladium-catalyzed cross-coupling reactions.
