Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Chem Rec. 2011 Dec;11(6):331-57. doi: 10.1002/tcr.201100018. Epub 2011 Nov 24.
Catalytic insertion or addition of a metal-imido/nitrene species, generated from reaction of a transition-metal catalyst with iminoiodanes, to C-H and C=C bonds offers a convenient and atom economical method for the synthesis of nitrogen-containing compounds. Following this groundbreaking discovery during the second half of the last century, the field has received an immense amount of attention with a myriad of impressive metal-mediated methods for the synthesis of amines and aziridines having been developed. This review will cover the significant progress made in improving the efficiency, versatility and stereocontrol of this important reaction. This will include the various iminoiodanes, their in situ formation, and metal catalysts that could be employed and new ligands, both chiral and non-chiral, which have been designed, as well as the application of this functional group transformation to natural product synthesis and the preparation of bioactive compounds of current therapeutic interest.
金属亚胺/氮宾物种的催化插入或加成，由过渡金属催化剂与亚胺碘烷反应生成，为含氮化合物的合成提供了一种方便且原子经济性的方法。在本世纪下半叶这一开创性发现之后，该领域受到了极大的关注，开发了许多令人印象深刻的金属介导方法来合成胺和氮杂环丙烷。这篇综述将涵盖在提高这一重要反应的效率、多功能性和立体选择性方面取得的重大进展。这将包括各种亚胺碘烷、它们的原位形成以及可采用的金属催化剂、新的配体，包括手性和非手性配体，以及该官能团转化在天然产物合成和当前治疗相关生物活性化合物制备中的应用。
