Haloalkyne Chemistry (eBook)

Huanfeng Jiang, Chuanle Zhu, Wanqing Wu (Autoren)

eBook Download: PDF

2015 | 1st ed. 2016
X, 77 Seiten
Springer Berlin (Verlag)
978-3-662-49001-3 (ISBN)

Infos

This book presents efficient and practical methods for the synthesis of various functionalized organic molecules from haloalkynes through different reaction processes such as cross-coupling reactions, nucleophilic additions and cycloadditions. It consists of four chapters demonstrating interesting examples of these transformations, and showcasing the synthetic power of haloalkynes for rapid assembly of complex molecular structures. Most of the protocols allow multiple bond-forming events to occur in a single operation, offering opportunities to advance chemical synthesis and address the increasing demands for green and sustainable chemistry. It also presents a wide range of functionalized products, including many synthetically useful conjugated cyclic and acyclic structures that have potential applications in materials science, chemical biology and natural product synthesis. This book is a valuable reference not only for organic chemists, but also for biologists and materials scientists involved in the modern synthesis of organic compounds and materials.

Huanfeng Jiang and Wanqing Wu are both Professors at the School of Chemistry and Chemical Engineering, South China University of Technology, China.

Chuanle Zhu is a Postdoctoral Fellow at the School of Chemistry and Chemical Engineering, South China University of Technology, China.

Prof. Huanfeng Jiang received his B.Sc. in chemistry from Hubei University in 1983, M.S. with Professor Lun Zhang at Wuhan University in 1990 and Ph.D. with Professor Xiyan Lu at the Shanghai Institute of Organic Chemistry, CAS in 1993. Then he joined Guangzhou Institute of Chemistry, CAS, as a research fellow. He became an Associate Professor in 1995 and a full Professor in 1998. In 2003, he moved to the South China University of Technology (SCUT), where he is currently the leading Professor of Chemistry. He received many awards, including Chinese Chemical Society-BASF Young Investigator's Award (2002), National Natural Science Funds for Distinguished Young Scholar (2006) and Asian Core Program Lectureship Award (2014). His research interests include synthetic methodology, green and sustainable chemistry. He was elected as a council member of Chinese Chemical Society in 2011.

Dr. Chuanle Zhu received his B.S. from Tianjin University in 2009 before obtaining his Ph.D. at the same university with Professor Junan Ma in 2014. He received the EIFFEL scholarship in 2011 and spent ten months (September 2011 to July 2012) as a visiting Ph.D. student in Professor Dominique Cahard' group at INSA de Rouen, France. In 2015, he joined SCUT and is currently a postdoctoral fellow with Professor Huanfeng Jiang. His research work is focused on the development and applications of new synthetic methods.

Prof. Wanqing Wu received

her B.S. in chemistry from Hunan University in 2005, and Ph.D. from Peking University in organic chemistry with Professors Zhen Yang and Chi-Sing Lee in 2010. She then joined the SCUT as a postdoctoral fellow with Professor Huanfeng Jiang. She was promoted to Associate Professor in 2012 and Professor in 2014. Her research focuses on the development of synthetic methodologies and their applications towards synthesis of natural products and functional materials.

Inhalt

Preface 6
Contents 8
Abbreviations 9
1 Introduction 11
Abstract 11
References 14
2 Preparation of Haloalkynes 15
Abstract 15
References 17
3 Reactions of Haloalkynes 18
Abstract 18
3.1 Transformations of Carbon-Halo Bond Motif 18
3.1.1 Construction of Carbon-Carbon Bond 19
3.1.1.1 Construction of C(sp)--C(sp) Bond 19
C(sp)--C(sp) Homo-Coupling 19
C(sp)--C(sp) Cross-Coupling 21
3.1.1.2 Construction of C(sp)--C(sp2) Bond 25
C(sp)--C(sp2) Cross-Coupling 25
Alkynylation Reactions 29
3.1.1.3 Construction of C(sp)--C(sp3) Bond 34
3.1.2 Construction of Carbon-Nitrogen Bond 42
3.1.3 Construction of Carbon-Sulfur Bond 44
3.1.4 Construction of Carbon-Phosphorus Bond 45
3.2 Transformations of Carbon-Carbon Triple Bond Motif 46
3.2.1 Nucleophilic Additions 47
3.2.1.1 Halogen Nucleophiles 47
3.2.1.2 Boron Nucleophiles 53
3.2.1.3 Carbon Nucleophiles 53
3.2.1.4 Nitrogen Nucleophiles 54
3.2.1.5 Oxygen Nucleophiles 55
3.2.1.6 Sulfur Nucleophiles 56
3.2.2 Cycloadditions 57
3.2.2.1 [2 + 2] Cycloaddition 57
3.2.2.2 [3 + 2] Cycloaddition 59
3.2.2.3 [4 + 2] and [2 + 2 + 2] Cycloadditions 65
3.3 Transformations Involved Both Carbon-Halo Bond and Carbon-Carbon Triple Bond Motif 66
3.3.1 Initially Reacted at the Carbon-Halo Bond 66
3.3.2 Initially Reacted at the Carbon-Carbon Triple Bond 69
References 74
4 Conclusions and Outlook 86
Abstract 86

Produkt-Details

• Erscheint lt. Verlag: 23.11.2015
• Reihe/Serie: SpringerBriefs in Green Chemistry for Sustainability
• Reihe/Serie: SpringerBriefs in Green Chemistry for Sustainability
• Reihe/Serie: SpringerBriefs in Molecular Science
• Reihe/Serie: SpringerBriefs in Molecular Science
• Zusatzinfo: X, 77 p. 73 illus., 69 illus. in color.
• Verlagsort: Berlin
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Biologie ► Biochemie
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik ► Elektrotechnik / Energietechnik
• Themenwelt: Technik ► Maschinenbau
• Schlagworte: Carbon-halo bond motif • cross-coupling • Cycloaddition • Haloalkyne • Homo-coupling • Nucleophilic addition • Transformation
• ISBN-10: 3-662-49001-3 / 3662490013
• ISBN-13: 978-3-662-49001-3 / 9783662490013