83465-27-4Relevant articles and documents
One-Pot Process to Carborano-Coumarin via Catalytic CascadeDehydrogenative Cross-Coupling
Au, Yik Ki,Lyu, Hairong,Quan, Yangjian,Xie, Zuowei
, (2020)
Ir-catalyzed cascade dehydrogenative CH/BH and BH/OH cross-coupling of carboranyl carboxylic acid with readily available benzoic acid has been achieved, leading to the facile synthesis of previously unavailable carborano-coumarin in a simple one-pot process. Two cage B—H, one aryl C—H and one O—H bonds are activated to construct efficiently new B—C and B—O bonds. The cascade cyclization can stop at the first B—H/C—H cross-coupling step by tuning the reaction conditions, resulting in a series of α-carboranyl benzoic acid and aryl carborane derivatives. Control experiments indicate that B—H/C—H dehydrocoupling proceeds preferentially over B—H/O—H dehydrocoupling, and both directing groups and oxidants are crucial for this reaction. An iridium(V) intermediate is proposed to be involved in the catalytic cycle.
One-Pot Sequential N-Heterocyclic Carbene/Rhodium(III) Catalysis: Synthesis of Fused Polycyclic Isocoumarins
Youn, So Won,Yoo, Huen Ji
supporting information, p. 2176 - 2183 (2017/07/07)
A one-pot sequential N-heterocyclic carbene–rhodium (NHC-Rh) catalysis is described, demonstrating the compatibility of NHC and Rh catalysts. N-Heterocyclic carbene-catalyzed aerobic oxidation of benzaldehydes and subsequent rhodium(III)-catalyzed oxidative coupling/annulation with multiple bonds enabled the formation of two C–O bonds and one C–C bond in a single pot. This operationally easy, one-pot protocol under air provides access to a diverse array of valuable fused polycyclic isocoumarins. (Figure presented.).
Synthesis of Phthalides through Tandem Rhodium-Catalyzed C–H Olefination and Annulation of Benzamides
Mishra, Neeraj Kumar,Park, Jihye,Choi, Miji,Sharma, Satyasheel,Jo, Hyeim,Jeong, Taejoo,Han, Sangil,Kim, Saegun,Kim, In Su
, p. 3076 - 3083 (2016/07/12)
The rhodium(III)-catalyzed tandem C–H olefination and cyclization of benzamides with various alkenes is described. This protocol provides direct access to highly substituted phthalides, which are known as crucial frameworks of biologically active compounds. In particular, the amide directing group containing a benzimidazole group facilitates the activation of aromatic ortho-C–H bonds leading to olefination intermediates, and is spantaneously converted into an acid moiety, which can further undergo the intramolecular annulation process.
