50597-88-1Relevant articles and documents
Protecting Group-Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions
Brittain, William D. G.,Cobb, Steven L.
, p. 6862 - 6871 (2020)
Being able to utilize a protecting group to influence remote regiocontrol offers a simple alternative approach to direct late-stage functionalization of complex organic molecules. However, protecting groups that have the ability to influence reaction regi
Facile and practical synthesis of π-extended oxepins by benzannulation and intramolecular cyclization
Umeda, Rui,Shimizu, Yuji,Ida, Yuta,Ikeshita, Masahiro,Suzuki, Shuichi,Naota, Takeshi,Nishiyama, Yutaka
, p. 183 - 186 (2018/12/11)
π-Extended oxepins 1 and dimer 8 were synthesized by the benzannulation of the corresponding asymmetric diarylacetylene derivatives and 2-(phenylethynyl)benzaldehyde followed by the Cu-catalyzed intramolecular cyclization. The optical properties of the π-extended oxepins 1 and 8 are also investigated.
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
supporting information, p. 11527 - 11536 (2017/08/30)
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
