Abstract
The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.
Highlights
Aryl derivatives of icosahedral carboranes C2 B10 H12 (Figure 1) are of interest for a wide variety of applications, starting with medical chemistry [1,2,3,4] and ending with the development of new materials [5,6,7,8,9,10,11,12]
K2 CO3 in acetone [44]; this approach gives only moderate yields of 9-aryl-ortho-carboranes and is not tolerant to many functional groups. In this contribution we describe convenient and mild synthesis of B-aryl derivatives of ortho-carborane containing various functional groups including ester and nitrile ones
The possibility of synthesis of B-aryl derivatives of ortho-carborane using organozinc reagents has been demonstrated earlier [40,41]. The preparation of these organozinc compounds was achieved by a transmetallation reaction of preformed organolithium or magnesium counterparts with zinc halide
Summary
Aryl derivatives of icosahedral carboranes C2 B10 H12 (Figure 1) are of interest for a wide variety of applications, starting with medical chemistry [1,2,3,4] and ending with the development of new materials [5,6,7,8,9,10,11,12]. This necessitates the development of new convenient methods for their synthesis.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
