69503-86-2Relevant academic research and scientific papers
High yielding alkylations of unactivated sp3 and sp2 centres with alkyl-9-BBN reagents using an NHC-based catalyst: Pd-PEPPSI-IPr
Valente, Cory,Baglione, Sylvia,Candito, David,O'Brien, Christopher J.,Organ, Michael G.
, p. 735 - 737 (2008/09/17)
High yielding, room temperature cross couplings of unactivated alkyl bromides and aryl bromides/chlorides with alkyl-9-BBN reagents has been achieved using an NHC-based catalyst (Pd-PEPPSI-IPr) via a general, functional-group tolerant and easily implemented protocol. The Royal Society of Chemistry.
Copper-Mediated, Palladium-Catalyzed Coupling of Thiol Esters with Aliphatic Organoboron Reagents
Yu, Ying,Liebeskind, Lanny S.
, p. 3554 - 3557 (2007/10/03)
Thiol esters and B-alkyl-9-BBN derivatives couple in the presence of a copper(I) carboxylate mediator and a palladium catalyst. In contrast to copper-mediated, palladium-catalyzed cross-couplings of thioorganics with boronic acids, the current coupling reaction of 9-BBN derivatives is facilitated by the addition of a base such as Cs2CO3. Under optimized conditions, a variety of thiol esters react with different B-alkyl-9-BBN derivatives giving ketones in moderate to excellent yields.
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 (2007/10/03)
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.
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.
