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Cleavage of C(aryl)-CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions.
Dai, Peng-Fei; Ning, Xiao-Shan; Wang, Hua; Cui, Xian-Chao; Liu, Jie; Qu, Jian-Ping; Kang, Yan-Biao.
Afiliación
  • Dai PF; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, China.
  • Ning XS; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, China.
  • Wang H; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, China.
  • Cui XC; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, China.
  • Liu J; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, China.
  • Qu JP; Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing, 211816, China.
  • Kang YB; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, China.
Angew Chem Int Ed Engl ; 58(16): 5392-5395, 2019 Apr 08.
Article en En | MEDLINE | ID: mdl-30821884
Organic chemists now can construct carbon-carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon-carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)-CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania