期刊
CHEMCATCHEM
卷 14, 期 16, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202200440
关键词
Suzuki Coupling; Nickel Bromide; Catalysis; Polycyclic Aromatic Hydrocarbons; Photophysical Properties
资金
- Science and Engineering Research Board [DST-SERB CRG/2018/000607]
- Scheme for Transformational and Advanced Research in Sciences, Ministry of Education [STARS/APR2019/CS/629/FS]
- Board of Research in Nuclear Sciences, Department of Atomic Energy [BRNS-DAE 37(2)/20/13/2016]
- Ministry of Electronics and Information Technology via the INUP-I2I program [5(1)/2021-NANO]
- Indian Council of Medical Research, New Delhi [5/3/8/20/2019-ITR]
Readily available and inexpensive bromide salt based on earth-abundant nickel has been used as a catalyst for the Suzuki coupling of various aryl halides with good yields and functional group tolerance under ambient conditions. The reaction follows a Ni(0)/Ni(II) catalytic cycle, where the oxidative addition of the aryl halide to Ni(0) is likely the rate-determining step.
Readily available and inexpensive bromide salt based on earth-abundant nickel has been used to catalyze the Suzuki coupling of a variety of aryl halides (ca. 37 examples) in high yields under ambient conditions with good functional group tolerance. The reactivity of various aryl halides follows the corresponding C-X (X=I, Br and Cl) bond strength in the order Ar-I>Ar-Br>Ar-Cl. EPR analysis, mercury-drop experiments and reactions with radical scavenger such as TEMPO point to the involvement of well-defined molecular species that operate via a Ni(0)/Ni(II) catalytic cycle where oxidative addition of the aryl halide to Ni(0) is likely to be the rate-determining-step (RDS). For the first time, valuable new polycyclic aromatic hydrocarbons (PAHs) with exciting photophysical properties have been synthesized (ca. 23 examples) via a Ni(II) catalyzed multi-fold Suzuki coupling.
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