2019
DOI: 10.1021/jacs.9b03375
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Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

Abstract: C–C bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C–C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to all… Show more

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Cited by 78 publications
(62 citation statements)
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“…Young used CO 2 as a transient directing group for several C-H functionalisation reactions, 65 including C(sp 2 )-H arylation of primary and secondary benzylamines (Scheme 20b). 66 Based on preliminary mechanistic investigation, the role of CO 2 was primarily to promote the formation of a carbamic acid in situ as both a protecting and directing group. Additionally, this process may prevent the formation of inactive palladium diamine complexes which is a hurdle all palladium catalysed amine functionalisation strategies must overcome.…”
Section: C(sp 2 )-H Functionalisation Of Aminesmentioning
confidence: 99%
“…Young used CO 2 as a transient directing group for several C-H functionalisation reactions, 65 including C(sp 2 )-H arylation of primary and secondary benzylamines (Scheme 20b). 66 Based on preliminary mechanistic investigation, the role of CO 2 was primarily to promote the formation of a carbamic acid in situ as both a protecting and directing group. Additionally, this process may prevent the formation of inactive palladium diamine complexes which is a hurdle all palladium catalysed amine functionalisation strategies must overcome.…”
Section: C(sp 2 )-H Functionalisation Of Aminesmentioning
confidence: 99%
“…[9][10][11] As amine derivatives are continuously finding their ways into new applications, scientists are looking for pathways to achieve complex amine-containing scaffolds (Figure 1). [12][13][14] Traditional approaches for the synthesis and derivatization of amines [15][16][17] are no longer the first choice as they lag behind when it comes to the synthesis as well as modification of amines with various active sites and number of functional groups. Simple protocols and sustainable approaches with the capability to functionalize the amine feedstocks into complex structures in a reduced number of steps are highly desirable to expedite the synthesis of amines.…”
Section: Introductionmentioning
confidence: 99%
“…Carbon dioxide (CO 2 ) is a thermodynamically stable and kinetic inert molecule however utilization and functionalization of CO 2 found many unique modes of actions [1,2]. For example, CO 2 can be used as temporary protecting group, thus preventing polymerization of acrylonitriles initiated by cyanide anion [3,4]. In principle, the nucleophilicity of cyanide is sufficiently high however it requires catalytic species to enhance reaction rates under controlled manner to improve selectivity [5].…”
Section: Introductionmentioning
confidence: 99%