Ruthenium-Catalyzed trans-Selective Hydrostannation of Alkynes

被引：91

作者：

Rummelt, Stephan M. ^{[1
]}

Fuerstner, Alois ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 14期

关键词：

alkynes; reaction mechanisms; ruthenium; synthetic methods; tin; CARBON TRIPLE BONDS; PROPARGYL ALCOHOLS; INTERNAL ALKYNES; TRIPHENYLTIN HYDRIDE; COMPLEXES; HYDROSTANNYLATION; METAL; HYDROSILYLATION; ACETYLENES; MECHANISM;

D O I：

10.1002/anie.201311080

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In contrast to all other transition-metal-catalyzed hydrostannation reactions documented in the literature, the addition of Bu3SnH across various types of alkynes proceeds with excellent trans selectivity, provided the reaction is catalyzed by [Cp*Ru]-based complexes. This method is distinguished by a broad substrate scope and a remarkable compatibility with functional groups, including various substituents that would neither survive under the conditions of established Lewis acid mediated trans hydrostannations nor withstand free-radical reactions. In case of unsymmetrical alkynes, a cooperative effect between the proper catalyst and protic functionality in the substrate allows outstanding levels of regioselectivity to be secured as well.

引用

页码：3626 / 3630

页数：5

共 71 条

[11]

Crabtree R. H., 1993, ANGEW CHEM, V105, P828

[12]

CRABTREE RH, 1993, ANGEW CHEM INT EDIT, V32, P789, DOI 10.1002/anie.199307891

[13] Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated α-triphenylstannylalkenes [J].

Dimopoulos, P ;

George, J ;

Tocher, DA ;

Manaviazar, S ;

Hale, KJ .

ORGANIC LETTERS, 2005, 7 (24) :5377-5380

[14] Ligand-Controlled Remarkable Regio- and Stereodivergence in Intermolecular Hydrosilylation of Internal Alkynes: Experimental and Theoretical Studies [J].

Ding, Shengtao ;

Song, Li-Juan ;

Chung, Lung Wa ;

Zhang, Xinhao ;

Sun, Jianwei ;

Wu, Yun-Dong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (37) :13835-13842

[15] Reactions of Alkynes with [RuCl(cyclopentadienyl)] Complexes: The Important First Steps [J].

Dutta, Barnali ;

Curchod, Basile F. E. ;

Campomanes, Pablo ;

Solari, Euro ;

Scopelliti, Rosario ;

Rothlisberger, Ursula ;

Severin, Kay .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (28) :8400-8409

[16] STRUCTURE AND CHEMISTRY OF THE COMPLEX TETRAKIS(ETA-5-PENTAMETHYLCYCLOPENTADIENYL)TETRAKIS(MU-3-CHLORO)-TETRARUTHENIUM(II) - A USEFUL PRECURSOR TO (PENTAMETHYLCYCLOPENTADIENYL)RUTHENIUM(0), (PENTAMETHYLCYCLOPENTADIENYL)RUTHENIUM(II), AND (PENTAMETHYLCYCLOPENTADIENYL)RUTHENIUM(IV) COMPLEXES [J].

FAGAN, PJ ;

MAHONEY, WS ;

CALABRESE, JC ;

WILLIAMS, ID .

ORGANOMETALLICS, 1990, 9 (06) :1843-1852

[17]

Farina V., 1997, ORG REACT, V50, P1

[18] Transition metal η2-vinyl complexes [J].

Frohnapfel, DS ;

Templeton, JL .

COORDINATION CHEMISTRY REVIEWS, 2000, 206 :199-235

[19] A versatile protocol for Stille-Migita cross coupling reactions [J].

Fuerstner, Alois ;

Funel, Jacques-Alexis ;

Tremblay, Martin ;

Bouchez, Laure C. ;

Nevado, Cristina ;

Waser, Mario ;

Ackerstaff, Jens ;

Stimson, Christopher C. .

CHEMICAL COMMUNICATIONS, 2008, (25) :2873-2875

[20] Total synthesis of myxovirescin A1 [J].

Fuerstner, Alois ;

Bonnekessel, Melanie ;

Blank, Jarred T. ;

Radkowski, Karin ;

Seidel, Guenter ;

Lacombe, Fabrice ;

Gabor, Barbara ;

Mynott, Richard .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (31) :8762-8783

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