Regioselective aromatic borylation in an inert solvent

被引:123
作者
Tse, MK [1 ]
Cho, JY [1 ]
Smith, MR [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
关键词
D O I
10.1021/ol0162668
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A protocol for performing Rh catalyzed aromatic borylations in cyclohexane has been devised. Borylation at the 5-position of several 1,3-substituted aromatic species ranging from electron-rich (1,3-(NMe2)(2)C6H4) to electron-deficient (1,3-(CF3)(2)C6H4) yields the corresponding aryl boronate esters. Veratrole was selectively borylated at the 4-position, thus extending regloselectivity to 1,2-substituted benzenes. Selective borylation at the 3-position of an N-protected pyrrole has also been demonstrated, providing a valuable reagent for cross-coupling reactions in a single step.
引用
收藏
页码:2831 / 2833
页数:3
相关论文
共 20 条
[1]   SYNTHESIS OF 3-ARYLPYRROLES AND 3-PYRROLYLACETYLENES BY PALLADIUM-CATALYZED COUPLING REACTIONS [J].
ALVAREZ, A ;
GUZMAN, A ;
RUIZ, A ;
VELARDE, E ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1653-1656
[2]   Highly regio- and stereoselective thermal migration of organoboranes in acyclic molecules [J].
Bromm, LO ;
Laaziri, H ;
Lhermitte, F ;
Harms, K ;
Knochel, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :10218-10219
[3]   Thermal, catalytic, regiospecific functionalization of alkanes [J].
Chen, HY ;
Schlecht, S ;
Semple, TC ;
Hartwig, JF .
SCIENCE, 2000, 287 (5460) :1995-1997
[4]   Steric and chelate directing effects in aromatic borylation [J].
Cho, JY ;
Iverson, CN ;
Smith, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12868-12869
[5]   Simple and rapid visual sensing of saccharides [J].
Davis, CJ ;
Lewis, PT ;
McCarroll, ME ;
Read, MW ;
Cueto, R ;
Strongin, RM .
ORGANIC LETTERS, 1999, 1 (02) :331-334
[6]   Catalytic C-H bond functionalization: Synthesis of arylsilanes by dehydrogenative transfer coupling of arenes and triethylsilane [J].
Ezbiansky, K ;
Djurovich, PI ;
LaForest, M ;
Sinning, DJ ;
Zayes, R ;
Berry, DH .
ORGANOMETALLICS, 1998, 17 (08) :1455-1457
[7]  
FUJITA K, 1991, Patent No. 9124021
[8]   PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].
ISHIYAMA, T ;
MURATA, M ;
MIYAURA, N .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510
[9]   Chemistry of Group 13 element-transition metal linkage - the platinum- and palladium-catalyzed reactions of (alkoxo)diborons [J].
Ishiyama, T ;
Miyaura, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 611 (1-2) :392-402
[10]   Stoichiometric and catalytic B-C bond formation from unactivated hydrocarbons and boranes [J].
Iverson, CN ;
Smith, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7696-7697