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AMVN-initiated expedient synthesis of biaryls by the coupling reaction of unactivated arenes and heteroarenes with aryl iodides
被引:36
作者:
Bhakuni, Bhagat Singh
[1
]
Yadav, Abhimanyu
[1
]
Kumar, Shailesh
[1
]
Kumar, Sangit
[1
]
机构:
[1] Indian Inst Sci Educ & Res IISER Bhopal, Dept Chem, Indore Bypass Rd, Bhopal 462066, Madhya Pradesh, India
关键词:
C-H-ARYLATION;
INTRAMOLECULAR ARYLATION;
MEDIATED SYNTHESIS;
ARYLBORONIC ACIDS;
HIGHLY EFFICIENT;
BUTOXIDE;
HETEROCYCLES;
ALKALOIDS;
CHLORIDES;
PYRIDINES;
D O I:
10.1039/c3nj01105d
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
The role of radical initiators AMVN and AIBN has been studied in the potassium tert-butoxide mediated biaryl coupling reaction of aryl iodides with unactivated arenes. Radical initiator AMVN promoted carbon-carbon bond formation expeditiously from aryl iodide having various groups such as amino, methoxy, fluoro, methyl, and trifluoromethyl and arenes in the presence of potassium tert-butoxide (4 equiv.) at 110 degrees C in 2-5 h. Substituted arenes such as toluene, xylene, anisole, and fluorobenzene also proceeded to form biaryls under AMVN-initiated reaction conditions. Moreover naphthalene, pyridine, pyrimidine, and pyridazine also coupled with aryl iodides and produced biaryls in 41-82% yields. It seems that AMVN initiates the formation of the aryl radical, which enters the radical chain reaction. The generated aryl radical may combine with the arene leading to a biaryl radical, which upon protonation gives the biphenyl radical anion and tert-butanol. The biphenyl radical anion finally reacts with the aryl iodide generating the aryl radical and thus completes the radical chain reaction with concomitant release of biphenyl.
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页码:827 / 836
页数:10
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