AK-2215GR_published_mainmanuscript

AK-2215GR_published_mainmanuscript - Issue in Honor of...

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Issue in Honor of Prof. Alain Krief ARKIVOC 2007 (x) 152-231 Metalated heterocycles in organic synthesis: recent applications Rafael Chinchilla,* Carmen Nájera,* and Miguel Yus* Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apartado 99, 03080 Alicante, Spain E-mails: chinchilla@ua.es , cnajera@ua.es , yus@ua.es Dedicated to Professor Alain Krief on occasion of his 65th birthday Contents 1. Introduction 2. Group 1 Metalated Heterocycles 2.1. Lithium heterocycles 2.1.1. Aromatic five-membered rings 2.1.2. Aromatic six-membered rings 2.1.3. Nonaromatic heterocyles 3. Group 2 Metalated Heterocycles 3.1. Magnesium heterocycles 3.1.1. Aromatic five-membered rings 3.1.2. Aromatic six-membered rings 3.1.3. Nonaromatic heterocyles 4. Group 3 Metalated Heterocycles 4.1. Boron heterocycles 4.1.1. Aromatic five-membered rings 4.1.2. Aromatic six-membered rings 4.1.3. Nonaromatic heterocyles 5. Group 4 Metalated Heterocycles 5.1. Silicon heterocycles 5.1.1. Aromatic five-membered rings 5.1.2. Aromatic six-membered rings 5.1.3. Nonaromatic heterocyles 5.2. Germanium Heterocycles 5.3. Tin Heterocycles 5.3.1. Aromatic five-membered rings 5.3.2. Aromatic six-membered rings 5.3.3. Nonaromatic heterocyles 6. Group 5 Metalated Heterocycles 6.1. Selenium heterocycles ISSN 1424-6376 Page 152 © ARKAT-USA, Inc.
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Issue in Honor of Prof. Alain Krief ARKIVOC 2007 (x) 152-231 6.2. Tellurium heterocycles 7. Transition-Metal-Substituted Heterocyles 7.1. Titanium heterocycles 7.2. Copper heterocycles 7.3. Zinc heterocycles 7.4. Mercury heterocycles 8. Conclusions 9. Acknowledgements 10. References 1. Introduction Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into an structure, probably the use of a metalated analogue is the most direct one. The present review deals with the generation and synthetic uses of organometallics formed by metalation of a heterocyclic ring, and can be considered as an update of our revision published in 2004 on this topic. 1 Therefore, only references published from the second quarter of 2003 until the third quarter of 2006 are included, and the same restrictions to the literature coverage applies. Thus, only metalated heterocycles which have found applicability are considered and transient metalated species forming part of a catalytic cycle are excluded. In addition, metalated species where the metal cannot be appropriately situated on a carbon but on a more electronegative atom after metalation due to, for instance, delocalization will also be excluded. As previously, 1 the present review is organized by the type of metal and subdivided by the type of metalated heterocycle, including methods for their preparation and their synthetic uses. 2. Group 1 Metalated Heterocycles 2.1. Lithium heterocycles Organolithiums keep their leading position as the most frequently employed metalated heterocycles, being useful on their own as nucleophiles or as the starting point in the preparation of many other metalated systems from less electropositive metals.
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This note was uploaded on 02/17/2011 for the course CHEMISTRY 101 taught by Professor Csr during the Spring '11 term at University of Louisville.

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AK-2215GR_published_mainmanuscript - Issue in Honor of...

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