Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB₁₁H₁₁]⁻

Abstract

The preparation of the carborane acid chloride [1-(COCl)–CB11H11]− from the carboxylic acid [1-(COOH)–CB11H11]− and subsequent amide formation are reported.

Highly selective palladium-catalyzed one-pot, five-fold B–H/C–H cross coupling of monocarboranes with alkenes

“…On the one hand, it can be transformed to the acid chloride, which in turn is a very useful functional group handle for the preparation of, e.g. , esters and amides 17. Product 3c was chosen as a representative example, and details about its clean conversion to the acid chloride 3c–Cl are provided in the ESI (p. S12) †.…”

Recent Progress in the Synthesis of the Monocarba‐closo‐dodecaborate(−) Anions

“…For example, they synthesized several compounds having amide directing groups 21 , 22 via acid chloride 20 . Remarkably, the acid chloride 20 was inert to moisture and could be stored under ambient conditions for several months (Scheme A) . The use of these amide directing groups in combination with iridium and rhodium catalysts enabled direct functionalization of the B2–6 vertices to give B−X (X=C, N, Cl) bonds (Scheme B) .…”

“…[21] For example, they synthesized severalc ompounds having amide directing groups 21, 22 via acid chloride 20.R emarkably, the acid chloride 20 was inert to moisture and could be stored under ambient conditions for severalm onths (Scheme7A). [22] The use of these amide directing groups in combination with iridium and rhodiumc atalysts enabledd irectf unctionalization of the B2-6 vertices to give BÀ X( X= C, N, Cl) bonds (Scheme 7B). [21c] As ak ey intermediate of BÀHa ctivation, an iridium complex [Et 4 N]·24 with ad irect BÀIr interaction was isolated;t he BÀIr bond was converted to aB À Xb ond, and the product 25 was fully characterized by X-ray crystallographic analysis( Scheme 7C).…”