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

被引：149

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

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1993年 / 462卷 / 1-2期

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.

引用

页码：19 / 29

页数：11

共 36 条

[1]

AMES DE, 1981, SYNTHESIS-STUTTGART, P364

[2]

[Anonymous], INT J POLYM MAT

[3] POLYMERS AND CERAMICS BASED ON ICOSAHEDRAL CARBORANES - MODEL STUDIES OF THE FORMATION AND HYDROLYTIC STABILITY OF ARYL ETHER, KETONE, AMIDE AND BORANE LINKAGES BETWEEN CARBORANE UNITS [J].