A convenient and genuine equivalent to HZrCp2Cl generated in situ from ZrCp2Cl2-DIBAL-H

被引:149
作者
Huang, Zhihong [1 ]
Negishi, Ei-ichi [1 ]
机构
[1] Purdue Univ, Herbert C Brown Labs Chem, W Lafayette, IN 47907 USA
关键词
D O I
10.1021/ol061202o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Slow addition of 1 equiv of (Bu2AlH)-Bu-i to ZrCp2Cl2 in THF provides a convenient route to either HZrCp2Cl-(Bu2AlCl)-Bu-i (Reagent I) or HZrCp2Cl (Reagents II and III). The latter represents a highly convenient route to genuine HZrCp2Cl, while Reagent I is useful for regio- and stereoselective conversion of 1- and 2-alkynes into (E)-1-iodo-1-alkenes and (E)-2-iodo-2-alkenes, respectively.
引用
收藏
页码:3675 / 3678
页数:4
相关论文
共 20 条
[1]   A MODIFIED PROCEDURE FOR THE PREPARATION OF CP2ZR(H)CL (SCHWARTZ REAGENT) [J].
BUCHWALD, SL ;
LAMAIRE, SJ ;
NIELSEN, RB ;
WATSON, BT ;
KING, SM .
TETRAHEDRON LETTERS, 1987, 28 (34) :3895-3898
[2]   PREPARATION OF ORGANOALUMINUM COMPOUNDS BY HYDROZIRCONATION-TRANSMETALATION [J].
CARR, DB ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) :3521-3531
[3]   STUDIES ON HYDROMETALATION REACTIONS - AN IMPROVED HYDROZIRCONATION REAGENT AND THE STRUCTURE OF A (MECP)2ZRCL(ALKENYL) CARBONYLATION PRODUCT [J].
ERKER, G ;
SCHLUND, R ;
KRUGER, C .
ORGANOMETALLICS, 1989, 8 (10) :2349-2355
[4]   HYDROZIRCONATION ORGANIC SYNTHESIS VIA ORGANOZIRCONIUM INTERMEDIATES - SYNTHESIS AND REARRANGEMENT OF ALKYLZIRCONIUM(IV) COMPLEXES AND THEIR REACTION WITH ELECTROPHILES [J].
HART, DW ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8115-8116
[5]   HYDROZIRCONATION .3. STEREOSPECIFIC AND REGIOSELECTIVE FUNCTIONALIZATION OF ALKYLACETYLENES VIA VINYLZIRCONIUM(IV) INTERMEDIATES [J].
HART, DW ;
BLACKBURN, TF ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :679-680
[6]  
Lipshutz BH, 2002, TITANIUM AND ZIRCONIUM IN ORGANIC SYNTHESIS, P110, DOI 10.1002/3527600671.ch4
[7]   A NEW METHOD FOR THE INSITU GENERATION OF CP2ZR(H)CL (SCHWARTZ REAGENT) [J].
LIPSHUTZ, BH ;
KEIL, R ;
ELLSWORTH, EL .
TETRAHEDRON LETTERS, 1990, 31 (50) :7257-7260
[8]  
Makabe H, 1999, EUR J ORG CHEM, V1999, P969, DOI 10.1002/(SICI)1099-0690(199905)1999:5<969::AID-EJOC969>3.0.CO
[9]  
2-G
[10]   A NOVEL ZIRCONIUM-CATALYZED HYDROALUMINATION OF OLEFINS [J].
NEGISHI, E ;
YOSHIDA, T .
TETRAHEDRON LETTERS, 1980, 21 (16) :1501-1504