97641-43-5Relevant academic research and scientific papers
Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis
Wang, Wang,Ding, Chao,Li, Yangyang,Li, Zheqi,Li, Yuqiang,Peng, Long,Yin, Guoyin
, p. 4612 - 4616 (2019)
An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n-regioselectivity, has been achieved by nickel catalysis. The nitrogen-based ligand plays an essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α-position of boron, selective and decisive bond formation is favored at the benzylic position.
Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams
Zhou, Cong,Li, Miao,Sun, Jianwei,Cheng, Jiang,Sun, Song
supporting information, p. 2895 - 2899 (2021/05/05)
A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.
A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Smith, Emily G.,Cambeiro, Xacobe C.
supporting information, p. 5383 - 5388 (2021/07/26)
A photocatalytic method for the α-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the β-position. Simple scale-up is demonstrated under continuous flow conditions, highlighting the practicality of the method.
Hydroaminoalkylation of sterically hindered alkenes with: N, N -dimethyl anilines using a scandium catalyst
Su, Jianhong,Zhou, Yiqun,Xu, Xin
supporting information, p. 2013 - 2019 (2019/02/20)
An atom- and step-economical C(sp3)-H addition of N,N-dimethyl anilines to various sterically demanding 1,1- and 1,2-disubstituted alkenes has been achieved by using a simple β-diketiminato ligand supported scandium dialkyl complex in combinati
CAPTODATIVE SUBSTITUENT EFFECTS - XV. GENERALISATION OF BRIDGED DEHYDRODIMERISATION BY VARYING RADICOPHILES AND POLARITY OF ATTACKING RADICALS
Mignani, S.,Mereenyi, R.,Janousek, Z.,Viehe, H. G.
, p. 769 - 774 (2007/10/02)
Captodative olefins efficiently trap both electrophilic or nucleophilic radicals, i. e. various thiyl, acetyl, acetamidomethyl and N-methylanilinomethyl radicals.In the first three cases, good yields of adductdimers 4 are formed and these reactions are preparatively useful.In the last case when anilinomethyl radicals are formed at 140 deg C, also dismutation or double adduct 5 formation may occur depending on the choice of c and d groups in 2.
