109845-76-3Relevant articles and documents
Arylation and alkenylation of activated alkyl halides using sulfonamides
Greaney, Michael F.,Johnson, Stuart,Kovács, Ervin
supporting information, p. 3222 - 3224 (2020/03/23)
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.
Metal-Free β-Amino Alcohol Synthesis: A Two-step Smiles Rearrangement
Yang, Di,Xie, Cai-Xia,Wu, Xiao-Tian,Fei, Luo-Ran,Feng, Lei,Ma, Chen
supporting information, p. 14905 - 14915 (2020/11/13)
A novel method for the synthesis of β-amino alcohols has been demonstrated under mild reaction conditions with a broad scope via a two-step Smiles rearrangement. What is more, theoretical calculations have been performed to confirm the rationality of the mechanism. The method has been proved to be notably effective for N-arylated amino alcohols, which are difficult to synthesize by traditional methods.
Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines
Akram, Manjur O.,Das, Avishek,Chakrabarty, Indradweep,Patil, Nitin T.
supporting information, p. 8101 - 8105 (2019/10/11)
The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.
