Synthesis of bulky arylphosphanes by rhodium-catalyzed formal [2+2+2] cycloaddition reaction and their use as ligands

被引：10

作者：

Kobatake, Takayuki ^{[1
]}

Kondoh, Azusa ^{[1
]}

Yoshida, Suguru ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

Oshima, Koichiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2008年 / 3卷 / 8-9期

关键词：

amination; cross-coupling; cycloaddition; phosphanes; rhodium;

D O I：

10.1002/asia.200800102

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of 1-alkynylphosphane sulfides with 1,6- or 1,7-diynes in the presence of a cationic rhodium catalyst results in a formal [2+2+2] cycloaddition reaction to afford the corresponding aromatic phosphane sulfides. The aromatic rings formed in the cycloaddition naturally bear one or two substituents at the ortho positions to the phosphorus atom, which creates a sterically hindered environment around the phosphorus atom. The following desulfidation of the products is facile under radical conditions or with the aid of tris(dimethylamino)phosphane, providing the corresponding bulky phosphanes. Dicyclohexyl(2,6-diphenylaryl)phosphane, which is available through this sequence, proves to serve as an efficient ligand in palladium-catalyzed cross-coupling amination reactions.

引用

页码：1613 / 1619

页数：7

共 64 条

[11] Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].

Hayashi, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362

[12] Carbocupration of 1-alkynylphosphines followed by trapping with electrophiles [J].

Kanemura, Shigenari ;

Kondoh, Azusa ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

ORGANIC LETTERS, 2007, 9 (10) :2031-2033

[13] Simple, highly active palladium catalysts for ketone and malonate arylation: Dissecting the importance of chelation and steric hindrance [J].

Kawatsura, M ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (07) :1473-1478

[14] One-pot syntheses of sterically shielded phosphorus ligands by selective stepwise nucleophilic substitution at triphenyl phosphite [J].

Keller, J ;

Schlierf, C ;

Nolte, C ;

Mayer, P ;

Straub, BF .

SYNTHESIS-STUTTGART, 2006, 2 (02) :354-365

[15] Non-symmetrically substituted 1,1′-binaphthyls in enantioselective catalysis [J].

Kocovsky, P ;

Vyskocil, S ;

Smrcina, M .

CHEMICAL REVIEWS, 2003, 103 (08) :3213-3245

[16] Synthesis of bulky phosphines by rhodium-catalyzed formal [2+2+2] cycloaddition reactions of tethered diynes with 1-alkynylphosphine sulfides [J].

Kondoh, Azusa ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (22) :6996-+

[17] Palladium-catalyzed anti-hydrothiolation of 1-alkynylphosphines [J].

Kondoh, Azusa ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

ORGANIC LETTERS, 2007, 9 (07) :1383-1385

[18] Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes [J].

Kondoh, Azusa ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :4099-4104

[19] Preparation of chiral triarylphosphines by Pd-catalysed asymmetric P-C cross-coupling [J].

Korff, C ;

Helmchen, G .

CHEMICAL COMMUNICATIONS, 2004, (05) :530-531

[20] Transition metal catalyzed [2+2+2] cycloaddition and application in organic synthesis [J].

Kotha, S ;

Brahmachary, E ;

Lahiri, K .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) :4741-4767

← 1 2 3 4 5 6 7 →