Vol.:(0123456789)
Topics in Current Chemistry (2019) 377:38
https://doi.org/10.1007/s41061-019-0267-y
1 3
REVIEW
Enamine/Transition Metal Combined Catalysis: Catalytic
Transformations Involving Organometallic Electrophilic
Intermediates
Samson Afewerki
1
· Armando Córdova
1
Received: 29 July 2019 / Accepted: 5 November 2019 / Published online: 16 November 2019
© The Author(s) 2019
Abstract
The concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations
not accessible without this combination. The amine catalyst activates the carbonyl
compounds through the formation of a reactive nucleophilic enamine intermediate
and, in parallel, the transition metal activates a wide range of functionalities such
as allylic substrates through the formation of reactive electrophilic π-allyl-metal
complex. Since the first report of this strategy in 2006, considerable effort has been
devoted to the successful advancement of this technology. In this chapter, these findings are highlighted and discussed.
Keywords Combined catalysis · Enamine catalysis · Transition metal catalysis ·
Amino catalysis · Organocatalysis
1 Introduction
The use of a small organic molecule to transform a chemical reaction through a
catalytic approach (organocatalysis) has proved to be a very fruitful and widely
employed chemical strategy [1, 2]. In this context, the use of an amine catalyst for
the activation of ketones and aldehydes by the formation of enamine [3] or iminium [4] intermediates allows for a wide range of chemical transformations to proceed. These strategies become even more interesting and further broadened when
* Samson Afewerki
samson.afewerki20@gmail.com
* Armando Córdova
armando.cordova@miun.se
1
Department of Natural Sciences, Mid Sweden University, 851 70 Sundsvall, Sweden
1
Reprinted from the journal
Chapter 1 was originally published as Afewerki, S. & Córdova, A. Topics in Current Chemistry (2019)
377: 38. https://doi.org/10.1007/s41061-019-0267-y.
Topics in Current Chemistry (2019) 377:38
https://doi.org/10.1007/s41061-019-0267-y
1 3
REVIEW
Enamine/Transition Metal Combined Catalysis: Catalytic
Transformations Involving Organometallic Electrophilic
Intermediates
Samson Afewerki
1
· Armando Córdova
1
Received: 29 July 2019 / Accepted: 5 November 2019 / Published online: 16 November 2019
© The Author(s) 2019
Abstract
The concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations
not accessible without this combination. The amine catalyst activates the carbonyl
compounds through the formation of a reactive nucleophilic enamine intermediate
and, in parallel, the transition metal activates a wide range of functionalities such
as allylic substrates through the formation of reactive electrophilic π-allyl-metal
complex. Since the first report of this strategy in 2006, considerable effort has been
devoted to the successful advancement of this technology. In this chapter, these findings are highlighted and discussed.
Keywords Combined catalysis · Enamine catalysis · Transition metal catalysis ·
Amino catalysis · Organocatalysis
1 Introduction
The use of a small organic molecule to transform a chemical reaction through a
catalytic approach (organocatalysis) has proved to be a very fruitful and widely
employed chemical strategy [1, 2]. In this context, the use of an amine catalyst for
the activation of ketones and aldehydes by the formation of enamine [3] or iminium [4] intermediates allows for a wide range of chemical transformations to proceed. These strategies become even more interesting and further broadened when
* Samson Afewerki
samson.afewerki20@gmail.com
* Armando Córdova
armando.cordova@miun.se
1
Department of Natural Sciences, Mid Sweden University, 851 70 Sundsvall, Sweden
1
Reprinted from the journal
Chapter 1 was originally published as Afewerki, S. & Córdova, A. Topics in Current Chemistry (2019)
377: 38. https://doi.org/10.1007/s41061-019-0267-y.