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.
引用
收藏
页码:827 / 836
页数:10
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