Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation was written by Kattamuri, Padmanabha V.;Yin, Jun;Siriwongsup, Surached;Kwon, Doo-Hyun;Ess, Daniel H.;Li, Qun;Li, Guigen;Yousufuddin, Muhammed;Richardson, Paul F.;Sutton, Scott C.;Kurti, Laszlo. And the article was included in Journal of the American Chemical Society in 2017.Application In Synthesis of 4-Bromo-2,6-difluoroanisole This article mentions the following:
Given the importance of amines in a large number of biol. active natural products, active pharmaceutical ingredients, agrochems., and functional materials, the development of efficient C-N bond-forming methods with wide substrate scope continues to be at the frontier of research in synthetic organic chem. Here, authors present a general and fundamentally new synthetic approach for the direct, transition-metal-free preparation of sym. and unsym. diaryl-, arylalkyl-, and dialkylamines that relies on the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable electrophilic aminating agents. Practical single and double polarity reversal (i.e., umpolung) of the nitrogen atom is achieved using sterically and electronically tunable ketomalonate-derived imines and oximes. Overall, this novel approach represents an operationally simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed C-N cross-coupling methods that are currently used to access structurally diverse secondary amines. In the experiment, the researchers used many compounds, for example, 4-Bromo-2,6-difluoroanisole (cas: 104197-14-0Application In Synthesis of 4-Bromo-2,6-difluoroanisole).
4-Bromo-2,6-difluoroanisole (cas: 104197-14-0) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Application In Synthesis of 4-Bromo-2,6-difluoroanisole
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem