钯催化邻-碳硼烷基吡啶卤化物交叉偶联合成邻-碳硼烷基联芳、氨基吡啶和炔基吡啶衍生物

Pd-Catalyzed Cross-Coupling of o-Carboranyl Pyridyl Halides:Synthesis of o-Carboranyl Biaryls,Aminopyridines and Alkynylpyridine Derivatives

发展了一种钯催化邻-碳硼烷基吡啶卤化物与(杂)芳基硼酸交叉偶联反应合成邻-碳硼烷基联芳衍生物的高效方法.该方法具有条件温和、官能团兼容性好等特点.此外,通过Buchwald-Hartwig反应及Sonogashira反应分别合成了邻-碳硼烷基氨基吡啶和炔基吡啶类化合物.该类杂环芳基碳硼烷衍生物在发光材料以及药物等领域具有应用潜力.

The Suzuki cross-coupling reaction between readily available o-carboranyl-substituted pyridyl halides and(hetero)arylboronic acids under Pd catalysis has been developed,providing access to o-carboranyl biaryls in yields of 35%~92%.The transformations proceed under mild conditions and with high functional group tolerance using commercially available coupling partners.Furthermore,the Buchwald-Hartwig reaction and Sonogashira reaction of o-carboranyl pyridyl halides are reported as well,leading to the facile synthesis of o-carboranyl aminopyridines and alkynylpyridine derivatives,respectively.It is believed that these heteroarylated carborane derivatives may find applications in luminescent materials and drug discovery.