Highly Functionalized Ferrocenes,European Journal of Inorganic Chemistry

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Highly Functionalized Ferrocenes
European Journal of Inorganic Chemistry ( IF 2.2 ) Pub Date : 2020-01-23 , DOI: 10.1002/ejic.201901183
Emmanuel Lerayer ₁ , Léa Radal ₁ , Tuan Anh Nguyen ₁ , Nejib Dwadnia ₁ , Hélène Cattey ₁ , Régine Amardeil ₁ , Nadine Pirio ₁ , Julien Roger ₁ , Jean-Cyrille Hierso _{1,

2}

Affiliation

Ferrocene is unique among organometallic compounds, and serves notably as a versatile platform towards the production of ligands useful to promote transition metals chemistry. A general limiting aspect of the synthesis of ferrocene derivatives is the efficient access to sophisticated highly functionalized polysubstituted ferrocenes, i.e. bearing four or more substituents replacing hydrogen atoms on the cyclopentadienyl rings. These ferrocene derivatives can bear various functional or/and structuring spectator substituents. Their preparation involves synthetic difficulties resulting from the need of multiple functionalizations coexisting altogether, and satisfying functional group compatibility and high selectivity issues. In the last decades, our group initially designed highly functionalized polyphosphines and hybrid ligands (1,1',3,3'‐tetrafunctionalized Fc) using dialkylated 1,1'‐tert‐butylferrocene as a scaffold, which opened the way to various new classes of hybrid compounds. Some of these original ferrocenes were used as ligands, promoting metal catalysed C–C and C–X bond formation (X = O, S, N, etc.). Thus, highly functionalized ferrocenes, which include notably (P,P,P,P)‐, (P,P,N,N)‐, (P,P,P')‐, (P,P,B)‐, (P,B)‐ and (N,B)‐compounds were developed in which the heteroatoms coexist in a close proximity on a common ferrocene platform with a controlled conformation. The present review details the concepts attached to the synthesis of these highly functionalized ferrocene species, and illustrates their main features and applications related to organometallic chemistry directed towards organic synthesis by metal catalysis.

中文翻译：

高度官能化的二茂铁

二茂铁在有机金属化合物中是独特的，并且显着地用作通向制备用于促进过渡金属化学的配体的通用平台。二茂铁衍生物合成的一般限制方面是有效地获得复杂的高度官能化的多取代的二茂铁，即带有四个或更多个取代环戊二烯基环上的氢原子的取代基。这些二茂铁衍生物可以带有各种功能或/和结构的旁观者取代基。它们的制备涉及由于共存的多种官能化的需要而导致的合成困难，并且满足官能团的相容性和高选择性的问题。在过去的几十年中，我们小组最初设计了高度功能化的多膦和杂化配体（1,1'，3,3'叔丁基二茂铁作为支架，为各种新型杂化化合物开辟了道路。这些原始的二茂铁中的一些用作配体，促进了金属催化的C–C和C–X键的形成（X = O，S，N等）。因此，高度官能化的二茂铁主要包括（P，P，P，P）‐，（P，P，N，N）‐，（P，P，P'）‐，（P，P，B）‐，开发了（P，B）-和（N，B）-化合物，其中杂原子紧密共存于具有受控构象的普通二茂铁平台上。本综述详细介绍了这些高度官能化的二茂铁物种的合成所涉及的概念，并阐明了它们的主要特征和与通过金属催化进行有机合成的有机金属化学有关的应用。

更新日期：2020-01-23

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