Organic Reactions, Volume 100

Written by a "who is who" of leading organic chemists, this anniversary volume represent the Organic Reactions editors' choice of the most important, ground-breaking and versatile reactions in current organic synthesis. The 15 reaction types selected for this volume include reactions for carbon-carbon bond formation, cross-coupling reactions, hydro- and halofunctionalizations, among many others.
In line with the successful recipe of the series, each chapter is focused on a single reaction, discussing its mechanism and stereochemistry, scope and limitations, applications to synthesis, comparison with other methods, and experimental procedures. Each chapter concludes with a tabular survey of selected key application examples, complete with reported reaction conditions and yields, to serve as a quick reference guide for synthesis planning.

1. The Negishi Cross-Coupling Reaction 1
Colin Diner and Michael G. Organ

2. Generation and Trapping of Functionalized Aryl- and Heteroarylmagnesium and -Zinc Compounds 63
Ferdinand H. Lutter, Maximilian S. Hofmayer, Jeffrey M. Hammann, Vladimir Malakhov, and Paul Knochel

3. Copper-Catalyzed, Enantioselective Hydrofunctionalization of Alkenes 121
Haoxuan Wang and Stephen L. Buchwald

4. The Catalytic, Enantioselective Favorskii Reaction: in Situ Formation of Metal Alkynylides and Their Additions to Aldehydes 207
Yeshua Sempere and Erick M. Carreira

5. Enantioselective Lithiation–Substitution of Nitrogen-Containing Heterocycles 255
Kevin Kasten, Nico Seling, and Peter O’Brien

6. Catalytic, Enantioselective, Transfer Hydrogenation 329
Masahiro Yoshimura and Masato Kitamura

7. Hydrofunctionalization of Alkenes by Hydrogen-Atom Transfer 383
Ryan A. Shenvi, Jeishla L. M. Matos, and Samantha A. Green

8. Carbon–Carbon Bond Formation by Metallaphotoredox Catalysis 471
Eric D. Nacsa and David W. C. MacMillan

9. Suzuki–Miyaura Cross-Coupling 547
Alexander B. Pagett and Guy C. Lloyd-Jones

10. ortho-Directed C–H Alkylation of Substituted Benzenes 621
Yusuke Ano and Naoto Chatani

11. Catalytic, Enantioselective, C–H Functionalization to Form Carbon–Carbon Bonds 671
Qing-Feng Wu, Gang Chen, Jian He, and Jin-Quan Yu

12. Catalytic, Enantioselective Fluorination Reactions 749
Richard T. Thornbury and F. Dean Toste

13. Catalyst-Controlled Glycosylation 801
Samuel M. Levi and Eric N. Jacobsen

14. Palladium-Catalyzed Amination of Aryl Halides 853
John F. Hartwig, Kevin H. Shaughnessy, Shashank Shekhar, and Rebecca A. Green

15. Catalytic, Enantioselective, Copper–Boryl Additions to Alkenes 959
Amir H. Hoveyda, Ming Joo Koh, Kyunga Lee, and Jaehee Lee

Cumulative Chapter Titles by Volume 1057

Author Index, Volumes 1–100 1075

Chapter and Topic Index, Volumes 1–100 1083

SCOTT E. DENMARK is the Reynold C. Fuson Professor of Chemistry at the University of Illinois at Urbana-Champaign. He has pioneered the concept of chiral Lewis base activation of Lewis acids for catalysis in main group synthetic organic chemistry. His group has also developed palladium-catalyzed cross-couplings with organofunctional silicon compounds. He has won a number of honors including the Pedler and Robert Robinson Medals, the Aldrich Award for Creative Work in Synthetic Organic Chemistry and the Prelog Medal. He was a founding editor of the Encyclopedia of Reagents for Organic Synthesis and served as Editor in Chief of Organic Reactions from 2008 to 2018. He is a member of the American Academy of Arts and Sciences and the National Academy of Sciences.

With contributions by

Colin Diner and Michael G. Organ

Paul Knochel, Ferdinand H. Lutter, Maximilian S. Hofmayer, Jeffrey M. Hammann, and Vladimir Malakhov

Haoxuan Wang and Stephen L. Buchwald

Yeshua Sempere and Erick M. Carreira

Kevin Kasten, Nico Seling, and Peter O'Brien

Masahiro Yoshimura and Masato Kitamura

Ryan A. Shenvi, Jeishla L. M. Matos, and Samantha A. Green

Eric D. Nacsa and David W. C. MacMillan

Alexander B. Pagett and Guy C. Lloyd-Jones

Yusuke Ano and Naoto Chatani

Qing-Feng Wu, Gang Chen, Jian He, and Jin-Quan Yu

Richard T. Thornbury and F. Dean Toste

Samuel M. Levi and Eric N. Jacobsen

John F. Hartwig, Kevin H. Shaughnessy, Shashank Shekhar, and Rebecca A. Green

Amir H. Hoveyda, Ming Joo Koh, Kyunga Lee, and Jaehee Lee