54885-00-6Relevant articles and documents
Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes
Lee, Shao-Chi,Li, Li-Yun,Tsai, Zong-Nan,Lee, Yi-Hsin,Tsao, Yong-Ting,Huang, Pin-Gong,Cheng, Cheng-Ku,Lin, Heng-Bo,Chen, Ting-Wei,Yang, Chung-Hsin,Chiu, Cheng-Chau,Liao, Hsuan-Hung
, p. 85 - 89 (2022/01/04)
Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.
Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis
Lei, Chuanhu,Zhu, Daoyong,Tangcueco, Vicente Iii Tiu,Zhou, Jianrong Steve
supporting information, p. 5817 - 5822 (2019/08/26)
A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.
Oxidant-Controlled C-sp2/sp3-H Cross-Dehydrogenative Coupling of N-Heterocycles with Benzylamines
Sharma, Rohit,Abdullaha, Mohd,Bharate, Sandip B.
, p. 9786 - 9793 (2017/09/23)
Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp2 or sp3 carbon resulted in the formation of C-benzoylated or alkenylated products. Benzoylation of N-heterocycles occurs via (NH4)2S2O8 catalyzed benzoyl radical formation. An oxidative alkenylation of N-heterocycles having C-sp3 carbon (2-methylaza-arenes) occurs via deamination of benzylamine followed by C-sp3-H bond activation in high stereoselectivity. Both benzoylation and alkenylation protocols are metal-free, green, simple, efficient, and tolerate a wide variety of functional groups.