Ruthenium-catalyzed reductive coupling reaction of propargylic alcohols via hydroboration of allenylidene intermediates

被引：39

作者：

Onodera, G

Nishibayashi, Y ^{[1
]}

Uemura, S

机构：

[1] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan

[2] Univ Tokyo, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan

来源：

ORGANOMETALLICS | 2006年 / 25卷 / 01期

关键词：

D O I：

10.1021/om0509241

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel ruthenium-catalyzed reductive coupling reaction of propargylic alcohols has been found to afford the corresponding 1,5-hexodiynes in good yields with high stereo-selectivity. This catalytic reaction may proceed via hydroboration the initially Of; produced ruthenium-allenylidene intermediates with pinacolborane as a key step, disclosing a new reactivity of the allenylidene complexes.

引用

收藏

页码：35 / 37

页数：3

相关论文

共 41 条

[1] Synergistic dimetallic effects in propargylic substitution reaction catalyzed by thiolate-bridged diruthenium complex [J].

Ammal, SC ;

Yoshikai, N ;

Inada, Y ;

Nishibayashi, Y ;

Nakamura, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (26) :9428-9438

[2] FACILE REACTION OF B-ALKYLBORACYCLANES WITH ALPHA,BETA-UNSATURATED CARBONYL DERIVATIVES - EXTENSION OF 1,4-ADDITION REACTION VIA ORGANOBORANES TO HIGHLY BRANCHED SECONDARY AND TERTIARY ALKYL GROUPS [J].

BROWN, HC ;

NEGISHI, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (15) :3777-&

[3] Transition metal complexes containing allenylidene, cumulenylidene, and related ligands [J].

Bruce, MI .

CHEMICAL REVIEWS, 1998, 98 (08) :2797-2858

[4]

Cadierno V, 2001, EUR J INORG CHEM, P571

[5] Ruthenium-catalyzed propargylic substitution reaction of propargylic alcohols with thiols: A general synthetic route to propargylic sulfides [J].

Inada, Y ;

Nishibayashi, Y ;

Hidai, M ;

Uemura, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15172-15173

[6] 2,5-bis(diphenylmethylene)-3-cyclopentenone: a solvent-dependent cobalt cluster mediated propargyl radical coupling process [J].

Kaldis, JH ;

McGlinchey, MJ .

TETRAHEDRON LETTERS, 2002, 43 (22) :4049-4053

[7] Spontaneous generation and stereoselective coupling of Co2(CO)6-complexed propargyl radicals [J].

Melikyan, GG ;

Villena, F ;

Sepanian, S ;

Pulido, M ;

Sarkissian, H ;

Florut, A .

ORGANIC LETTERS, 2003, 5 (19) :3395-3397

[8] A NOVEL SYNTHETIC APPROACH TO CYCLOOCTA-1,5-DIYNES AND CYCLOOCT-3-ENE-1,5-DIYNES VIA COBALT-COMPLEXED PROPARGYL RADICALS [J].

MELIKYAN, GG ;

KHAN, MA ;

NICHOLAS, KM .

ORGANOMETALLICS, 1995, 14 (05) :2170-2172

[9] Cobalt-templated radical processes: inter- and intramolecular coupling of propargyl radicals [J].

Melikyan, GG ;

Deravakian, A ;

Myer, S ;

Yadegar, S ;

Hardcastle, KI ;

Ciurash, J ;

Toure, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 578 (1-2) :68-75

[10] A NOVEL AND EFFICIENT SYNTHESIS OF CYCLIC AND ACYCLIC 1,5-ALKADIYNES BY SELECTIVE COUPLING OF CO-2(CO)(6)-COMPLEXED PROPARGYL RADICALS [J].

MELIKYAN, GG ;

COMBS, RC ;

LAMIRAND, J ;

KHAN, M ;

NICHOLAS, KM .

TETRAHEDRON LETTERS, 1994, 35 (03) :363-366

← 1 2 3 4 5 →