Ammonia as Ultimate Amino Source in Synthesis of Primary Amines via Nickel-Promoted C–H Bond Amination

Lin, Ying‐Chu; Yang, Chan; Yu, Yongqi; Li, Da; Hu, Liang; Xiao, Yuanjiu; Song, Zenan; Tan, Ze

doi:10.1021/acs.orglett.9b01968

Cited by 34 publications

(16 citation statements)

References 80 publications

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“…Nickel catalyzed ortho-selective CÀ H amination of amides using quinoline as a directing group. [39] Scheme 15. Copper-mediated aromatic CÀ H bond amination proposed by Kim et al [40] Scheme 16.…”

Section: Hydroamination Of Olefins Using Ammoniamentioning

confidence: 99%

Employing Ammonia for Diverse Amination Reactions: Recent Developments of Abundantly Available and Challenging Nitrogen Sources

et al. 2022

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Ammonia is the simplest molecule for the installation of nitrogen atom in organic compounds. It is abundantly available, economic and highly attractive from the point of atom economy for its use in organic synthesis, however, an highly challenging task for accessing the nitrogenous scaffolds through NÀ H activation of ammonia. With the advancement of synthetic procedures, scientific community continually developing excellent reactions employing ammonia as a source of nitrogen for various types of amination reactions and accomplishing the synthesis of nitrogenous compounds. This Review provides recent developments in amination reactions employing ammonia as a nitrogen source at a single platform.

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Section: Hydroamination Of Olefins Using Ammoniamentioning

confidence: 99%

Employing Ammonia for Diverse Amination Reactions: Recent Developments of Abundantly Available and Challenging Nitrogen Sources

et al. 2022

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“…该反应采用廉价的叠氮化钠作为胺化试剂, 可以兼容较多官能团, 如烯基、硝基、酯基等. 随后, 谭泽课题组 [112] 以氨气作为胺化试剂, 实现了镍催化的苯甲酰胺邻位碳氢键的胺化反应(Scheme 47, b). 在立体选择性方面, 仅有几例钴催化的不对称碳氢键胺化反应的例子被报道 [92,104] .…”

Section: 以羟胺及其衍生物为胺化试剂unclassified

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

Feng¹,

Shi²

2021

Chinese Journal of Organic Chemistry

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Nitrogen-containing organic compounds are ubiquitous in natural products, drug molecules and organic intermediates. Therefore, the introduction of nitrogenous functional groups into organic compounds is of great significance. Despite transition metalcatalyzed C-N coupling reaction provided an effcient strategy to access these ntrogen-containing compounds, extra steps are generally required to obtain the pre-functionalized starting materials. Recently, transi-tionmetalcatalyzed C-H amination has emerged as a more atom-and step-economical strategy to construct C-N bonds. Compared to the noble metals (e.g. palladium and rhodium), base metal catalysts, such as copper, cobalt and nickel, have attracted dramatic attentions, due to their earth abundance, cost effectiveness, and unique catalytic activities. Herein, the recent advances in copper-, cobalt-and nickel-catalyzed C-H amination reactions assisted by directing groups were summmarized according to the types of base metals, C-H bonds, and amination reagents with an emphasis on the discussion of various amination reagents and their application. Finally, the limitations and development trend of this research field are analyzed and prospected.

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“…Among these studies, the C−H activation reaction has attracted more attention, which provided an efficient route to form C−N bonds without prefunctionalized substrates and atom‐economy [2] . In this field, many groups have made great achievements, in the presence of metal catalysts to develop analogous reactions by the directing group (DG) assisted C−H activation reaction [3a–g] . Additionally, organic electrosynthesis has become a new and powerful strategy for the C−H functionalization reaction [3h–j] .…”

Section: Introductionmentioning

confidence: 99%

Ni(II)‐Mediated Ortho C(sp2)‐H Amidation of Arenes to Synthesis Secondary Sulfonamides via Sulfonyl Azides

Shi

et al. 2021

ChemistrySelect

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In this paper, we described Ni(II)-mediated C(sp 2 )À H amidation of arenes directed by an amide-tethered oxazoline directing group. The method provides a direct easy manner to achieve sulfonamides derivatives by available sulfonyl azides as amine source. The protocol exhibited moderate yields and functional group compatibility. Additionally, Synthetic amide compound has the Aggregation-Induced Emission (AIE) phenomenon, which exhibit the potential application in OLEDs field.

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Ammonia as Ultimate Amino Source in Synthesis of Primary Amines via Nickel-Promoted C–H Bond Amination

Cited by 34 publications

References 80 publications

Employing Ammonia for Diverse Amination Reactions: Recent Developments of Abundantly Available and Challenging Nitrogen Sources

Employing Ammonia for Diverse Amination Reactions: Recent Developments of Abundantly Available and Challenging Nitrogen Sources

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

Ni(II)‐Mediated Ortho C(sp2)‐H Amidation of Arenes to Synthesis Secondary Sulfonamides via Sulfonyl Azides

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