Iridium-catalyzed [3+2] annulation of 1,3-dienes with ortho-carbonylated phenylboronic acids.: A catalytic process involving regioselective 1,2-addition

被引：38

作者：

Nishimura, Takahiro ^{[1
]}

Yasuhara, Yuichi ^{[1
]}

Hayashi, Tamio ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 24期

关键词：

D O I：

10.1021/ja072369v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Annulation of 1,3-dienes with 2-formylphenylboronic acid proceeded with high regio- and stereoselectivity in the presence of a hydroxoiridium catalyst to give high yields of indanol derivatives. Various 1,3-dienes bearing electron-withdrawing and -donating substituents were successfully used under the catalytic conditions.

引用

页码：7506 / +

页数：3

共 16 条

[1] X-RAY CRYSTALLOGRAPHIC STUDIES ON FLUXIONAL PENTACOORDINATE TRANSITION-METAL COMPLEXES .1. (CYCLOOCTA-1,5-DIENE)BIS(DIMETHYLPHENYLPHOSPHINO)METHYLIRIDIUM(I) [J].

CHURCHILL, MR ;

BEZMAN, SA .

INORGANIC CHEMISTRY, 1972, 11 (09) :2243-+

[2] SYNTHESIS, CHARACTERIZATION, AND REACTIVITY OF ALKOXIDE AND HYDROXIDE COMPLEXES OF RHODIUM(I) AND IRIDIUM(I) [J].

GREEN, LM ;

MEEK, DW .

ORGANOMETALLICS, 1989, 8 (03) :659-666

[3] A novel catalysis of [{IrCl(cod)}2] complex in organic syntheses [J].

Ishii, Y ;

Sakaguchi, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (05) :909-920

[4] Novel and highly regio- and stereoselective nickel-catalyzed homoallylation of benzaldehyde with 1,3-dienes [J].

Kimura, M ;

Ezoe, A ;

Shibata, K ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4033-4034

[5] Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes [J].

Kimura, Masanari ;

Ezoe, Akihiro ;

Mori, Masahiko ;

Iwata, Keisuke ;

Tamaru, Yoshinao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8559-8568

[6] Rhodium-catalyzed tandem cyclization:: Formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media [J].

Lautens, M ;

Marquardt, T .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4607-4614

[7] Addition of bifunctional organoboron reagents to strained alkenes. Carbon-carbon bond formation with Rh(I) catalysis in aqueous media [J].

Lautens, M ;

Mancuso, J .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3478-3487

[8] Diastereoselective formation of indanes from arylboronate esters catalyzed by rhodium(I) in aqueous media [J].

Lautens, M ;

Mancuso, J .

ORGANIC LETTERS, 2002, 4 (12) :2105-2108

[9] Synthesis of 1H-inden-1-ol derivatives via rhodium-catalyzed annulation of o-acylphenylboronic acids with alkynes [J].

Matsuda, T ;

Makino, M ;

Murakami, M .

CHEMISTRY LETTERS, 2005, 34 (10) :1416-1417

[10] Rhodium-catalyzed annulation reactions of 2-cyanophenylboronic acid with alkynes and strained alkenes [J].

Miura, T ;

Murakami, M .

ORGANIC LETTERS, 2005, 7 (15) :3339-3341

← 1 2 →