65161-16-2Relevant academic research and scientific papers
Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
Wang, Gaonan,Gan, Yi,Liu, Yuanhong
supporting information, p. 916 - 920 (2018/09/22)
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.
Regioselective and stereospecific cross-coupling of primary allylic amines with boronic acids and boronates through palladium-catalyzed C-N bond cleavage
Li, Man-Bo,Wang, Yong,Tian, Shi-Kai
supporting information; experimental part, p. 2968 - 2971 (2012/04/18)
The NH2 group serves as an effective leaving group in the palladium-catalyzed regioselective and stereospecific title reaction (see scheme). The reaction works well with aryl- and alkenylboronic acids and aryl-, alkenyl-, allyl-, and benzylboronates, and complete transfer of chirality has been achieved when using α-chiral primary allylic amines as the allylic electrophiles. Copyright
Cross-coupling of N-allylic sulfonimides with organozinc reagents at room temperature
Tang, Xiang-Ling,Wu, Zhao,Li, Man-Bo,Gu, Yonghong,Tian, Shi-Kai
, p. 4107 - 4109 (2012/09/08)
An efficient cross-coupling reaction of N-allylic sulfonimides with organozinc reagents has been developed. In the presence of 1 mol-% of Pd 2(dba)3, a range of N-allylic sulfonimides smoothly couple with various organozinc reagents at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive α-selectivity. It is noteworthy that allyl ether, benzyl ether, and ester are tolerated under the reaction conditions. A range of N-allylic sulfonimides smoothly couple with various organozinc reagents in the presence of 1 mol-% of Pd2(dba)3 at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive α-selectivity.
Palladium-catalyzed cross-couplings of allylic carbonates with triarylbismuths as multi-coupling atom-efficient organometallic nucleophiles
Rao, Maddali L.N.,Banerjee, Debasis,Giri, Somnath
experimental part, p. 1518 - 1525 (2010/08/03)
Allylic carbonates were efficiently cross-coupled with triarylbismuths under palladium catalysis. Using the optimized protocol, arylations of various allylic carbonates were carried out with triarylbismuths to afford high yields of 1,3-disubstituted prope
Enantioselective iridium-catalyzed allylic arylation
Polet, Damien,Rathgeb, Xavier,Falciola, Caroline A.,Langlois, Jean-Baptiste,El Hajjaji, Samir,Alexakis, Alexandre
supporting information; experimental part, p. 1205 - 1216 (2009/09/06)
We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.
Copper catalyzed magnesium-Barbier reaction for γ-selective alkyl-allyl coupling
Erdik, Ender,Ko?o?lu, Melike
, p. 4211 - 4214 (2008/02/08)
CuCN catalyzed alkyl-allyl coupling under magnesium-Barbier conditions occurs regioselectively and affords predominantly the γ-products in good to high yields. This one-pot CuCN catalyzed reaction utilising Mg, an alkyl halide and an allylic substrate in THF at room temperature provides an easy alternative to the classical CuCN catalyzed γ-allylation of alkyl Grignard reagents.
Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: Inversion of absolute configuration
Evans, P. Andrew,Uraguchi, Daisuke
, p. 7158 - 7159 (2007/10/03)
The transition metal-catalyzed allylic substitution with unstabilized carbon nucleophiles represents an important cross-coupling reaction for the construction of ternary carbon stereogenic centers. We have developed a new regio- and enantiospecific rhodium-catalyzed allylic alkylation of acyclic unsymmetrical chiral nonracemic allylic alcohol derivatives with aryl zinc bromides. This study demonstrates that the hydrotris(pyrazolyl)borate rhodium catalyst and zinc(II) halide salt are crucial for efficiency, while the addition of lithium bromide to the catalyst is necessary for obtaining optimal regiospecificity. The stereochemical course of this reaction was established through the synthesis of (S)-ibuprofen, which demonstrated that the alkylation proceeds with net inversion of absolute configuration consistent with direct addition of the nucleophile to the metal center followed by reductive elimination. Copyright
