Iron-Catalyzed 1,4-Hydroboration of 1,3-Dienes

被引：244

作者：

Wu, Jessica Y. ^{[1
]}

Moreau, Benoit ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 36期

关键词：

TRANSITION-METAL-COMPLEXES; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; ALLYLIC ALCOHOLS; ORGANIC-SYNTHESIS; LIGANDS; CYCLOISOMERIZATION; HYDROBORATIONS; CATECHOLBORANE; ALLYLBORATION;

D O I：

10.1021/ja9048493

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chemo-, regio-, and stereoselective iron-catalyzed 1,4-hydroboration of dienes that affords gamma-disubstituted allylboranes has been developed. 1,4-Hydroboration of 2-substituted dienes forms allylborane products with (E)-trisubstituted double bonds exclusively.

引用

页码：12915 / +

页数：4

共 48 条

[1] Platinum-catalyzed tandem diboration/intramolecular allylboration: Diastereoselective access to cyclohexanes bearing 1,3-diols [J].

Ballard, CE ;

Morken, JP .

SYNTHESIS-STUTTGART, 2004, (09) :1321-1324

[2]

BARTON DHR, 1983, CHEM COMMUN, P41

[3] Hydroborations catalysed by transition metal complexes [J].

Beletskaya, I ;

Pelter, A .

TETRAHEDRON, 1997, 53 (14) :4957-5026

[4]

BELLUCCI C, 1989, FARMACO, V44, P1167

[5] An octahedral coordination complex of iron(VI) [J].

Berry, John F. ;

Bill, Eckhard ;

Bothe, Eberhard ;

George, Serena DeBeer ;

Mienert, Bernd ;

Neese, Frank ;

Wieghardt, Karl .

SCIENCE, 2006, 312 (5782) :1937-1941

[6] ONE-POT SYNTHESIS OF PRECOCENE-I AND PRECOCENE-II AND A FORMAL SYNTHESIS OF ROBUSTADIAL-A AND ROBUSTADIAL-B VIA 2-PHENYL-4H-1,3,2-BENZODIOXABORIN [J].

BISSADA, S ;

LAU, CK ;

BERNSTEIN, MA ;

DUFRESNE, C .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (08) :1866-1869

[7] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[8] Iron-catalyzed [2π+2π] cycloaddition of α,ω-dienes:: The importance of redox-active supporting ligands [J].

Bouwkamp, Marco W. ;

Bowman, Amanda C. ;

Lobkovsky, Emil ;

Chirik, Paul J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13340-13341

[9]

BROWN HC, 2001, ORGANIC SYNTHESES VI, V2, P118

[10]

BROWN HC, 2001, ORGANIC SYNTHESES VI, V2, P189

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