C-ARYLATION AND C-HETEROARYLATION OF ICOSAHEDRAL CARBORANES VIA THEIR COPPER(I) DERIVATIVES

被引:148
作者
COULT, R [1 ]
FOX, MA [1 ]
GILL, WR [1 ]
HERBERTSON, PL [1 ]
MACBRIDE, JAH [1 ]
WADE, K [1 ]
机构
[1] UNIV DURHAM,DEPT CHEM,DURHAM DH1 3LE,ENGLAND
关键词
D O I
10.1016/0022-328X(93)83337-U
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reaction between C-mono- or C,C'-di-copper(I) derivatives of 1,2-, 1,7-, or 1,12-dicarba-closo-dodecaborane(12) and aryl iodides in the presence of pyridine gives the corresponding C-mono- or C,C'-diaryl derivatives of 1,7- and 1,12-dicarba-closo-dodecaboranes(12); 1,2-dicarba-closo-dodecaborane(12) gives only the C-monoaryl product. Cyclic or linear arylene coupled systems are obtained when di-iodoarenes are used. Copper(I) derivatives may be generated from C-unsubstituted or C-monosubstituted carboranes using copper(I) t-butoxide when substituents incompatible with the use of C-lithio-intermediates are involved. The C-copper(l) derivative of 1,2-dicarba-closo-dodecaborane(12) gives 1,2-di-2'-pyridyl-1,2-dicarba-closo-dode specifically with 2-bromopyridine. The (inferred) intermediate mono-2-pyridyl-derivative, obtained independently from 2-ethynylpyridine and the dimethylsulphide complex of decaborane, gives 1-phenyl-2,2'-pyridyl-1,2-dicarba-closo-dodecaborane(12) upon conversion into its copper(I) derivative and treatment with iododobenzene. However, the copper(I) derivative of 1-phenyl-1,2-dicarba-closo-dodecaborane(12) does not react to a significant extent with 2-bromopyridine.
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页码:19 / 29
页数:11
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