E- and Z-Selective Transfer Semihydrogenation of Alkynes Catalyzed by Standard Ruthenium Olefin Metathesis Catalysts

被引：71

作者：

Kusy, Rafal ^{[1
]}

Grela, Karol ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52,POB 58, PL-01224 Warsaw, Poland

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 23期

关键词：

STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; TANDEM CATALYSIS; E-ALKENES; REDUCTION;

D O I：

10.1021/acs.orglett.6b03254

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective transfer semihydrogenation of alkynes to yield alkenes was achieved with commercial first and second generation Hoveyda-Grubbs catalysts and formic acid as a hydrogen donor. This catalytic system is distinguished by its selectivity and compatibility with many functional groups (halogens, cyano, nitro, sulfide, alkenes). The metathetic activity of the ruthenium catalysts may be utilized in tandem sequences of olefin metathesis plus alkyne reduction.

引用

页码：6196 / 6199

页数：4

共 50 条

[21] Pyridine-Stabilized Fast-Initiating Ruthenium Monothiolate Catalysts for Z-Selective Olefin Metathesis
Occhipinti, Giovanni
Tornroos, Karl W.
Jensen, Vidar R.
ORGANOMETALLICS, 2017, 36 (17) : 3284 - 3292
[22] Theory-assisted design of Z-selective olefin metathesis catalysts
Occhipinti, Giovanni
Koudriavtsev, Vitali
Tornroos, Karl
Jensen, Vidar
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
[23] Pd-Catalyzed Z-Selective Semihydrogenation of Alkynes: Determining the Type of Active Species
Drost, Ruben M.
Rosar, Vera
Marta, Silvia Dalla
Lutz, Martin
Demitri, Nicola
Milani, Barbara
de Bruin, Bas
Elsevier, Cornelis J.
CHEMCATCHEM, 2015, 7 (14) : 2095 - 2107
[24] Simple and Highly Z-Selective Ruthenium-Based Olefin Metathesis Catalyst
Occhipinti, Giovanni
Hansen, Fredrik R.
Tornroos, Karl W.
Jensen, Vidar R.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (09) : 3331 - 3334
[25] Rationally designed Ru-based catalysts for Z-selective olefin metathesis
Khan, Rana Kashif M.
Hoveyda, Amir H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[26] Z-Selective Olefin Metathesis Processes Catalyzed by a Molybdenum Hexaisopropylterphenoxide Monopyrrolide Complex
Flook, Margaret M.
Jiang, Annie J.
Schrock, Richard R.
Mueller, Peter
Hoveyda, Amir H.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) : 7962 - +
[27] Z-selective olefin metathesis processes catalyzed by a molybdenum hexaisopropylterphenoxide monopyrrolide complex
Flook, Margaret M.
Jiang, Annie J.
Schrock, Richard R.
Müller, Peter
Hoveyda, Amir H.
Journal of the American Chemical Society, 2009, 131 (23): : 7962 - 7963
[28] Efficient Z-Selective Semihydrogenation of Internal Alkynes Catalyzed by Cationic Iron (II) Hydride Complexes
Gorgas, Nikolaus
Brunig, Rjulian
Stoger, Berthold
Vanicek, Stefan
Tilset, Mats
Veiros, Luis F.
Kirchner, Karl
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (43) : 17452 - 17458
[29] New ruthenium-based catalysts for Z-selective metathesis of hindered olefins
Quigley, Brendan L.
Grubbs, Robert H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[30] Z-Selective Cross Metathesis with Ruthenium Catalysts: Synthetic Applications and Mechanistic Implications
Herbert, Myles B.
Grubbs, Robert H.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (17) : 5018 - 5024

← 1 2 3 4 5 →