Chemical Synthesis

• To provide a solid, balanced and current training in chemical synthesis and in the theoretical tools that facilitate its success.
• Simultaneous and complementary learning of the most common synthetic strategies and tactics to provide students with a comprehensive and current view of this fundamental area of chemistry.
• To provide an overview of the methods of synthesis of individual molecules, libraries of organic molecules, organometallic complexes and inorganic compounds.
• Analysis of the available methodologies for performing asymmetric synthesis.
• To deepen the synthetic methodology used in the preparation of complex organic, inorganic and organometallic compounds.
• To develop skills that allow the future professional application of the knowledge provided.

1. Overview of the course
a. Synthesis of organic substances:
a.1. Target-Oriented synthesis (TOS)
a.2. Diversity-Oriented synthesis (DOS)
b. Synthesis of organometallic complexes
c. Synthesis of materials (MOF’s and COF’s)

2. Basic tools for the synthesis of organic compounds
a. Structure(s)
b. Reactions
c. Retrosynthetic analysis

3. Strategy
a. Target-Oriented synthesis
a.1. Transform-based strategies
a.2. Structure-based and topological strategies
a.3. Functional group-based strategies
a.4. Stereochemical strategies
a.5. Computer-Assisted Synthetic Planning: Human vs. Machine or Human + Machine?
b. Diversity-Oriented synthesis
b.1. Multicomponent reactions
b.2. Cycloaddition reactions
b.3. Tandem reactions
b.4. Functional group pairing strategies
b.5. Privileged structures
b.6. Ring-closing metathesis

4. Asymmetric Synthesis
a. Chiral pool
b. Chiral auxiliaries
c. Chiral catalysis

5. Synthesis of organometallic complexes
a. Necessity for the synthesis of organometallic complexes: preparation of metal catalysts and study of reaction mechanisms
b. Metal-X complexes
b.1. Hydrocarbyl (alkyl, aryl, vinyl) complexes
b.2. Pi-allyl complexes
b.3. Metal-hydride complexes
b.4. Metal-porphyrin, amido and alkoxo complexes
b.5. Metal-boryl complexes
c. Metal-carbene complexes
c.1. Types
c.2. Reactivity: metathesis
d. Metal imido and metal-oxo complexes: synthesis and applications (e.g. dioxygen and dinitrogen activation in biological systems; metalloenzymes)

6. Synthesis of MOF’s and COF’s
a. Definition and concept of MOF’s and COF’s
b. Synthetic strategies:
b.1. Metal geometry
b.2. Linkers
b.3. Design and control over pore size and functionality
c. Applications

BASIC (REFERENCE MANUALS).
• R. E. Gawley, J. Aubé;, Principles of Asymmetric Synthesis, 2nd Ed., Elsevier: Oxford, 2012.
• Asymmetric Synthesis, The Essentials, M. Christmann and S. Bräse, Eds. Wiley-VCH: Weinheim, 2007.
• J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd Ed., Oxford University Press: Oxford, 2012.
• S. G. Warren, P. Wyatt, Organic Synthesis: The Disconnection Approach, 2nd. Ed., Wiley, 2009.
• P. Wyatt, S. Warren, Organic Synthesis: Strategy and Control, Wiley, 2007.
• E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, 1989.
• A. Trabocchi, Ed., Diversity-Oriented Synthesis, Basics and Applications in Organic Synthesis, Drug Discovery and Chemical Biology, Wiley 2013.
COMPLEMENTARY.
• Enantioselective Organocatalysis: Reactions and Experimental Procedures, P. I. Dalko, Ed., Wiley-VCH: Weinheim, 2007.
• Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes, R. Rios Torres, Ed., John Wiley and Sons: New Jersey, 2013.
• Organic Synthesis Workbook, J. A. Gewert, J. Görlitzer, S. Götze, J. Looft, P. Menningen, T. Nöbel, H. Schirock, C. Wulff, Wiley- VCH: Weinheim, 2000.
• Organic Synthesis Workbook II, C. Bittner, A. S. Busemann, U. Griesbach, F. Haunert, W.-R. Krahnert, A. Modi, J. Olschimke, P. L. Steck, Wiley-VCH: Weinheim, 2001.

BASIC AND GENERAL COMPETENCES:
CB6: To possess and understand knowledge that provides a basis or opportunity to be original in the development and / or application of ideas, often in a research context.
CB7: That students know how to apply the knowledge acquired and their ability to solve problems in new or unfamiliar environments within broader (or multidisciplinary) contexts related to their area of study.
CB8: That students are able to integrate knowledge and face the complexity of making judgments based on information that, being incomplete or limited, includes reflections on social and ethical responsibilities linked to the application of their knowledge and judgments.
CB9: That students know how to communicate their conclusions and the knowledge and the ultimate reasons that sustain them to specialized and non-specialized audiences in a clear and unambiguous way.
CB10: That students have the learning skills that allow them to continue studying in a way that will be largely self-directed or autonomous.
CG2: To know how to apply the scientific method and to acquire skills in the elaboration of the necessary protocols for the design and critical evaluation of chemical experiments.
CG3: To be able to discuss and communicate their ideas, orally and in writing, to specialized and non-specialized public (congresses, etc.) in a clear and reasoned way.
CG5: To have the skills that allow the student to develop a mode of study and autonomous learning.
CG6: To have the ability for leadership, creativity, initiative and entrepreneurial spirit.
CG7: To be able to work as part of multidisciplinary teams and collaborate with other professionals, both nationally and internationally.
CG8: To be able to handle scientific bibliography and to develop the necessary criteria for its interpretation and management.
CG10: To be able to develop the different stages involved in a research (from conceiving an idea and doing a bibliographical search to the approach of the objectives, the design of the experiment, the analysis of the results and the deduction of the corresponding conclusions).
CG11: To be able to adapt efficiently to future doctoral studies in multidisciplinary areas
TRANSVERSAL COMPETENCES:
CT2: To elaborate, write and publicly defend scientific and technical reports.
CT3: To work autonomously and efficiently in the daily practice of research or professional activity.
CT4: To apply the concepts, principles, theories or models related to Biological Chemistry and Molecular Materials to new or little known environments, within multidisciplinary contexts.
CT5: To appreciate the value of quality and continuous improvement, acting with rigor, responsibility and professional ethics.
CT6: To be able to adapt to changes, being able to apply with initiative new and advanced technologies and other relevant developments.
CT7: To demonstrate critical and self-critical reasoning in search of scientific quality and rigor. To manage computer tools and information and communication technologies, as well as access to online databases.
SPECIFIC COMPETENCES:
CE20: To understand the necessity and importance of chemical synthesis.
CE21: To know the most relevant chemical synthesis methods, including the fundamentals of stereoselective processes in chemistry, and be able to design synthetic routes of complex molecules.

Theoretical lectures: lessons in the classroom, where the main concepts and theoretical contents of the course will be explained, using power point presentations and/or explanations on the board. Student participation will be encouraged by asking questions about the concepts explained. The contents of these lessons will be applied to solve exercises and problems during seminars.

Seminars: Support material will be provided by the teacher in advance. The student will try to solve the exercises before attending the seminars, where active student participation and discussion will be encouraged.

The student participates actively in different ways: preparation and presentation of individual works, delivery of exercises to the teacher, solving exercises in the classroom, etc. Attendance at these classes is mandatory.

Scheduled tutorials: Individual or group work for solving specific questions or problems about theory, problems, exercises, readings or other proposed tasks. They may be carried out partially telematically

In this scenario, expository and interactive teaching will be fundamentally of a face-to-face nature. Exceptionally, virtual teaching may be combined with face-to-face teaching up to a maximum of 10% of the hours of the subject.

The class attendance is mandatory and at least an 80% of it will be required to pass the course.

The evaluation of this course will be done by means of the continuous assessment and completion of a final exam.
The continuous evaluation will have a weight of 25% in the qualification of the subject, and will consist of three components: a) seminars (10%), b) reports (10%), c) attendance and participation (5%).

The final exam will cover all the contents of the subject and will have a weight of 75%.

The student's grade will not be lower than that of the final exam or that obtained by weighting with the continuous assessment.

The repeaters will have the same system of class attendance than those who study the course for the first time.

For each hour of lectures and seminars the student should dedicate two hours of autonomous work (study and consultation of books) to work with the acquired knowledge, both doing the exercises that are proposed and deepening the new concepts introduced.
The student will perform an individual or group work and perform a final written exam of about 3 hours. All this supposes a total of hours of work of the student to which it would be necessary to add the hours of tutoring.
In case of not passing the subject in the ordinary call, the written exam corresponding to the extraordinary call will also have an approximate duration of 3 hours.
PRESENTIAL WORK IN THE CLASSROOM
Face-to-face lectures: 14 h
Interactive classes in small groups (Seminars and practical classes of blackboard): 4 h
Tutoring in a small groups: 1 h
Oral presentations by the students 2 h
Exam: 3 h
Total hours classroom work in the classroom: 24 hours
PERSONAL WORK OF THE STUDENT (NON-PRESENTIAL)
Preparation of tests and directed works: 10 h
Self-study, individually or in group:s 36 h
Bibliographic searches and database use: 5 h
Total hours of personal work of the student: 51 h

It is recommended to pay special attention to the discussions about the basic tools of chemical synthesis, the utility of the different strategies and their applications. It is also important to review the subjects of other courses on organic, inorganic and organometallic chemistry.
Continuous monitoring of the subject of the course is recommended, weekly exercises and problems proposed, as well as participating in the preparation and presentation of a topic related to the content of the subject among those proposed by the teacher.