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© Springer-Verlag GmbH Germany, part of Springer Nature 2019
A. Lei (ed.), Transition Metal Catalyzed Oxidative Cross-Coupling Reactions,
Lecture Notes in Chemistry 102, https://doi.org/10.1007/978-3-662-58104-9_3
Chapter 3
Oxidative Coupling Reactions Between
Hydrocarbons and Organometallic
Reagents (The Second Generation)
Chuan He
3.1 Introduction
The oxidative coupling reactions between two organometallic reagents have greatly
enriched our approach toward synthetic disconnections as discussed in Chap. 2.
However, the organometallic reagents are often needed to be prepared through additional synthetic steps and lead to the formation of unwanted stoichiometric amounts
of chemical waste, which bring a significant environmental footprint. Nowadays,
the development of green, atom-economical, and sustainable methods to make molecules is becoming more and more important and imperative for organic chemists.
Thus, the possibility of construction of carbon–carbon and carbon–heteroatom
bonds via direct C–H bond transformation provides a highly attractive strategy in
modern organic synthesis, due to the ubiquitous nature of C–H bonds in various
hydrocarbons (alkynes, arenes, alkenes, and alkanes). In this light, C–H bond functionalization has become one of the most exciting and rapidly developing fields of
organic chemistry over the past 20 years or so [1]. With the efforts of many research
groups, huge successful results have been achieved in this area. This transformation
has become an established piece in the organic chemists’ toolbox and enables the
rapid construction and late-stage diversification of functional molecules [2–5].
Recently, by viewing C–H bonds as “nucleophiles”, the merge of C–H bond
functionalization with oxidative cross-coupling reactions opens a new chapter in
organic synthesis with many exciting opportunities. The reaction of C–H bonds
with another nucleophile, which could be either an organometallic reagent or
another hydrocarbon, gives rise to the second and third generation of oxidative
coupling reactions. In this chapter, we summarize the second-generation oxidative
C. He (*)
Department of Chemistry and Shenzhen Grubbs Institute,
Southern University of Science and Technology, Shenzhen, Guangdong, China
e-mail: hec@sustc.edu.cn
© Springer-Verlag GmbH Germany, part of Springer Nature 2019
A. Lei (ed.), Transition Metal Catalyzed Oxidative Cross-Coupling Reactions,
Lecture Notes in Chemistry 102, https://doi.org/10.1007/978-3-662-58104-9_3
Chapter 3
Oxidative Coupling Reactions Between
Hydrocarbons and Organometallic
Reagents (The Second Generation)
Chuan He
3.1 Introduction
The oxidative coupling reactions between two organometallic reagents have greatly
enriched our approach toward synthetic disconnections as discussed in Chap. 2.
However, the organometallic reagents are often needed to be prepared through additional synthetic steps and lead to the formation of unwanted stoichiometric amounts
of chemical waste, which bring a significant environmental footprint. Nowadays,
the development of green, atom-economical, and sustainable methods to make molecules is becoming more and more important and imperative for organic chemists.
Thus, the possibility of construction of carbon–carbon and carbon–heteroatom
bonds via direct C–H bond transformation provides a highly attractive strategy in
modern organic synthesis, due to the ubiquitous nature of C–H bonds in various
hydrocarbons (alkynes, arenes, alkenes, and alkanes). In this light, C–H bond functionalization has become one of the most exciting and rapidly developing fields of
organic chemistry over the past 20 years or so [1]. With the efforts of many research
groups, huge successful results have been achieved in this area. This transformation
has become an established piece in the organic chemists’ toolbox and enables the
rapid construction and late-stage diversification of functional molecules [2–5].
Recently, by viewing C–H bonds as “nucleophiles”, the merge of C–H bond
functionalization with oxidative cross-coupling reactions opens a new chapter in
organic synthesis with many exciting opportunities. The reaction of C–H bonds
with another nucleophile, which could be either an organometallic reagent or
another hydrocarbon, gives rise to the second and third generation of oxidative
coupling reactions. In this chapter, we summarize the second-generation oxidative
C. He (*)
Department of Chemistry and Shenzhen Grubbs Institute,
Southern University of Science and Technology, Shenzhen, Guangdong, China
e-mail: hec@sustc.edu.cn