30089-56-6Relevant academic research and scientific papers
Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters
Bercher, Olivia P.,Watson, Mary P.,Xu, Jianyu
, p. 8608 - 8613 (2021)
The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the naphthyl requirement that pervades stereospecific cross-couplings involving enantioenriched electrophiles.
Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands
Hu, Zhiyong,Wei, Xiao-Jing,Handelmann, Jens,Seitz, Ann-Katrin,Rodstein, Ilja,Gessner, Viktoria H.,Goo?en, Lukas J.
supporting information, p. 6778 - 6783 (2021/02/01)
The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.
Regiodivergent DH or HD Addition to Alkenes: Deuterohydrogenation versus Hydrodeuterogenation
Hilt, Gerhard,Li, Luomo
, (2020/03/03)
The regioselective and regiodivergent addition of H-D to a variety of 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. The reaction was initiated by catalytic amounts of B
Copper-Catalyzed Enantioconvergent Radical Suzuki-Miyaura C(sp3)-C(sp2) Cross-Coupling
Jiang, Sheng-Peng,Dong, Xiao-Yang,Gu, Qiang-Shuai,Ye, Liu,Li, Zhong-Liang,Liu, Xin-Yuan
supporting information, p. 19652 - 19659 (2020/12/01)
A copper-catalyzed enantioconvergent Suzuki-Miyaura C(sp3)-C(sp2) cross-coupling of various racemic alkyl halides with organoboronate esters has been established in high enantioselectivity. Critical to the success is the use of a chiral cinchona alkaloid-derived N,N,P-ligand for not only enhancing the reducing capability of copper catalyst to favor a stereoablative radical pathway over a stereospecific SN2-type process but also providing an ideal chiral environment to achieve the challenging enantiocontrol over the highly reactive radical species. The reaction has a broad scope with respect to both coupling partners, covering aryl- and heteroarylboronate esters, as well as benzyl-, heterobenzyl-, and propargyl bromides and chlorides with good functional group compatibility. Thus, it provides expedient access toward a range of useful enantioenriched skeletons featuring chiral tertiary benzylic stereocenters.
Nickel(0)-Catalyzed Hydroarylation of Styrenes and 1,3-Dienes with Organoboron Compounds
Xiao, Li-Jun,Cheng, Lei,Feng, Wei-Min,Li, Mao-Lin,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information, p. 461 - 464 (2018/02/21)
A Ni-catalyzed hydroarylation of styrenes and 1,3-dienes with organoboron compounds has been developed. The reaction offers a highly selective approach to diarylalkanes and allylarenes under redox-neutral conditions. In this hydroarylation reaction, a new strategy that uses the proton of methanol to generate the active catalyst species Ni?H was developed. The Ni-catalyzed hydroarylation, combined with a Ir-catalyzed C?H borylation, affords a very efficient and straightforward access to a retinoic acid receptor agonist.
Cu-Catalyzed Suzuki-Miyaura reactions of primary and secondary benzyl halides with arylboronates
Sun, Yan-Yan,Yi, Jun,Lu, Xi,Zhang, Zhen-Qi,Xiao, Bin,Fu, Yao
, p. 11060 - 11062 (2014/09/30)
A copper-catalyzed Suzuki-Miyaura coupling of benzyl halides with arylboronates is described. Varieties of primary benzyl halides as well as more challenging secondary benzyl halides with β hydrogens or steric hindrance could be successfully converted into the corresponding products. Thus it provides access to diarylmethanes, diarylethanes and triarylmethanes. This journal is the Partner Organisations 2014.
Palladium-catalyzed cross-coupling reaction of secondary benzylic bromides with grignard reagents
Lopez-Perez, Ana,Adrio, Javier,Carretero, Juan C.
supporting information; experimental part, p. 5514 - 5517 (2010/02/28)
"Chemical Equation Presented" A mild palladium-catalyzed Kumada-Corriu reaction of secondary benzylic bromides with aryl and alkenyl Grignard reagents has been developed. In the presence of the Xantphos ligand, the undesired β-elimination pathway Is minimized, affording the corresponding cross-coupling products In acceptable to good yields. The reaction proceeds with inversion of the configuration.
