13033-04-0Relevant articles and documents
Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcoholsviaC-H bond activation
Banerjee, Debasis,Bera, Sourajit,Kabadwal, Lalit Mohan
supporting information, p. 4777 - 4780 (2020/05/13)
The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping of the enamine intermediate1a'are of special importance.
Nickel-catalysed alkylation of C(sp3)-H bonds with alcohols: direct access to functionalised N-heteroaromatics
Vellakkaran, Mari,Das, Jagadish,Bera, Sourajit,Banerjee, Debasis
supporting information, p. 12369 - 12372 (2018/11/20)
The first base-metal catalysed coupling of primary alcohols with methyl-N-heteroaromatics is reported. The use of an earth abundant and nonprecious NiBr2/L1 system enables access to a series of C(sp3)-alkylated N-heteroaromatics. Mechanistic studies have established the participation of a hydrogen-borrowing strategy for α-alkylation.
The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation
Basnet, Prakash,Thapa, Surendra,Dickie, Diane A.,Giri, Ramesh
supporting information, p. 11072 - 11075 (2016/09/19)
We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.