CH3612 – Synthetic Methodology

Duration:

15 hours + 1 x 2 hour workshop

Lecturers:

Dr C. P. Johnston and Professor N. J. Westwood*

*Module Convenor

Aims:

To provide an extensive review of well-established methods in organic synthesis. A detailed understanding of sulfur, phosphorus, boron, silicon and transition metal chemistry will be developed. The further development of skills in understanding and describing reaction mechanisms forms a central part of this course.

Objectives:

It is hoped that on completion of this course a student will have an appreciation of the following:

The chemistry of organosulfur, organophosphorus, organoboron and organosilicon compounds including their synthesis and use in a variety of chemical transformations.
General reactivity trends for these 4 classes of compounds as well as examples of their role in specific/named reactions.
The strategic application of protecting groups in organic synthesis including their installation, removal, and stability.
The reactivity of the s-block and reactive transition metal organometallic reagents and how directing groups are used to expand their utility in synthesis. An understanding of the chemoselectivity of deprotonations of heteroatom-functionalised aromatics with alkyl lithium reagents.
The reactions used to prepare organo-s-block compounds, organozincs, and organocuprates, and their reactivity with functional groups including Weinreb amides, acid chlorides, nitriles, and other carbonyl derivatives.
The models used to predict the stereochemistry of attack of organometallics with α-chiral carbonyl compounds, including the Felkin-Anh model.
The reaction mechanisms and synthetic applications of Pd-catalysed reactions including: Kumada-Corriu, Negishi, Suzuki-Miyaura, Stille, Hiyama-Denmark, Buchwald-Hartwig, Mizoroki-Heck, and Sonogashira coupling reactions.
The reactivity and synthetic applications of Pd-catalysed C–H activation.
The reaction mechanisms and synthetic applications of metal catalysed olefin metathesis reactions.