Copper-Catalyzed Amination of Aryl and Alkenyl Electrophiles

by Kevin H. Shaughnessy, Engelbert Ciganek, Rebecca B. DeVasher

2017 · John Wiley & Sons

The metal-catalyzed amination of aryl and alkenyl electrophiles has developed into a widely used methodology for the synthesis of natural products, active pharmaceutical ingredients, agricultural chemicals, and materials for molecular electronics. Copper catalysts promote the coupling of a wide range of nitrogen nucleophiles, including amines, amides, and heteroaromatic nitrogen compounds with aryl and alkenyl halides. The reactivity profile of copper catalysts is complementary to that of palladium catalysts in many cases. Copper catalysts are highly effective with less nucleophilic nitrogen nucleophiles, such as amides and azoles, whereas palladium catalysts are more effective with more nucleophilic amine nucleophiles. Copper is an attractive alternative to palladium due to its significantly lower cost. In addition, high activity palladium catalysts require expensive and often air-sensitive ligands, whereas the modern copper systems use relatively stable and inexpensive diamine or amino acid ligands. Copper-catalyzed C N coupling reactions are tolerant of a wide range of functional groups and have been applied to the synthesis of a variety of complex natural products. Significant work has also been done to understand the mechanism of these reactions. Current mechanistic understanding of these methodologies is covered in this monograph. The contents of the book are taken from the comprehensive review of the topic in the Organic Reactions series. Optimal experimental conditions for the amination of aryl and alkenyl halides with all classes of nitrogen nucleophiles are presented. Specific experimental procedures from the literature are provided for the major classes of copper-catalyzed C N coupling reactions. A tabular survey of all examples of Cu-catalyzed arylation and alkenylation of nitrogen nucleophiles is presented in 35 tables organized by nitrogen nucleophile and electrophilic coupling partner. The literature is covered through December 2015 and provides 300 recent citations to supplement the 680 citations of the original hardbound chapter. These latest literature references have been collected in separate sections according to the sequence of the tables in the tabular survey section. In each of the sections, the individual citations have been arranged in alphabetic order of the author names. Copper-Catalyzed Amination of Aryl and Alkenyl Electrophiles is intended to provide organic chemists with an accessible, but detailed, introduction to this important class of transformations.

Biomimicry for Optimization, Control, and Automation

by Kevin M. Passino

2004 · Springer Science & Business Media

There are many highly effective optimization, feedback control, and automation systems embedded in living organisms and nature. Evolution persistently seeks optimal robust designs for biological feedback control systems and decision making processes. From this comprehensive text you will gain knowledge of how mimicry of such biological processes can be used to solve optimization, control, and automation problems encountered in the construction of high technology systems. Mathematical stability analysis is treated for a number of cases, from attentional systems to social foraging swarm cohesion properties. Bio-inspired optimization and control methods are compared to conventional techniques with an objective to provide a balanced viewpoint. • A companion web site, continually updated by the author, will provide you with further examples and design problems, solution hints, lecture slides, a running lab and ongoing self-study problems and resources. • MATLAB® code is provided to solve a number of key problems. • Focus lies on verifying correct operation of technologies via a process of mathematical modelling and analysis complimented by computer simulations. • Written from an engineering perspective, methods are applied to extensive real-world applications, from ship steering to cooperative control of a group of autonomous robots. Aimed primarily at graduate courses and research, much of the material has been successfully used for undergraduate courses. This dynamic textbook sends an injection of new ideas into engineering technology and the academic community.