Home / Articles / Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I

Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I

, 
Carmen Nájera 2
Carmen Nájera
, 
Miguel Yus 2
Miguel Yus
1 Lomonosov Moscow State University, Faculty of Chemistry
2 University of Alicante, Spain
Published 30 November 2019
34
Share
Cite this
GOST
 | 
Cite this
GOST
Beletskaya I. P., Nájera C., Yus M. Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I // Russian Chemical Reviews. 2019. Vol. 89. No. 2. pp. 250-274.
GOST all authors (up to 50)
Beletskaya I. P., Nájera C., Yus M. Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I // Russian Chemical Reviews. 2019. Vol. 89. No. 2. pp. 250-274.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RCR4916
UR - https://rcr.colab.ws/publications/10.1070/RCR4916
TI - Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I
T2 - Russian Chemical Reviews
AU - Beletskaya, Irina Petrovna
AU - Nájera, Carmen
AU - Yus, Miguel
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 250-274
IS - 2
VL - 89
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{2019_Beletskaya,
author = {Irina Petrovna Beletskaya and Carmen Nájera and Miguel Yus},
title = {Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4916},
number = {2},
pages = {250--274},
doi = {10.1070/RCR4916}
}
MLA
Cite this
MLA
Beletskaya, Irina Petrovna, et al. “Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part~I.” Russian Chemical Reviews, vol. 89, no. 2, Nov. 2019, pp. 250-274. https://rcr.colab.ws/publications/10.1070/RCR4916.
Views / Visits / Downloads
47 / 46 / 7

Abstract

The review presents state-of-the-art data on the influence of catalysts (mainly transition metal complexes) on the regioselectivity of a number of reactions. The most important addition reactions to unsaturated bonds are considered, in particular, hydroformylation, hydrosilylation, hydroboration and hydroxy-, alkoxy- and aminocarbonylation, which give predominantly one product. Particular attention is given to reactions with divergent regioselectivity. The reaction conditions, the structures of metal complexes and the ligands involved are indicated and, in some cases, the reaction mechanism is discussed. Examples of industrial processes using homogeneous catalysis are given.

The bibliography includes 203 references.

Funders

Russian Science Foundation
19-13-00223

References

1.
Divergent Catalytic Approach from Cyclic Oxime Esters to Nitrogen-Containing Heterocycles with Group 9 Metal Catalysts
Shimbayashi T., Matsushita G., Nanya A., Eguchi A., Okamoto K., Ohe K.
ACS Catalysis , 2018
2.
Site‐Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis
Okumura S., Komine T., Shigeki E., Semba K., Nakao Y.
Angewandte Chemie - International Edition , 2017
4.
Stereodivergent Catalysis
Beletskaya I.P., Nájera C., Yus M.
Chemical Reviews , 2018
5.
Stereodivergent Synthesis of Tetrahydrofuroindoles through Pd-Catalyzed Asymmetric Dearomative Formal [3+2] Cycloaddition
6.
rcr_89_2_250_bib6
Wiese
2006
7.
Applied Hydroformylation
Franke R., Selent D., Börner A.
Chemical Reviews , 2012
8.
rcr_89_2_250_bib8
Claver
2002
9.
Expanded Scope of Supported Aqueous Phase Catalysis: Efficient Rhodium-Catalyzed Hydroformylation of α,β-Unsaturated Esters
10.
Zwitterionic rhodium complexes as catalysts for the hydroformylation of olefins
Amer I., Alper H.
Journal of the American Chemical Society , 1990
14.
Highly Enantioselective Hydroformylation of Olefins Catalyzed by Rhodium(I) Complexes of New Chiral Phosphine−Phosphite Ligands
Nozaki K., Sakai N., Nanno T., Higashijima T., Mano S., Horiuchi T., Takaya H.
Journal of the American Chemical Society , 1997
19.
Hydroformylation of Internal Olefins to Linear Aldehydes with Novel Rhodium Catalysts
van der Veen L.A., Kamer P.C., van Leeuwen P.W.
Angewandte Chemie - International Edition , 1999
21.
rcr_89_2_250_bib21
2004
23.
rcr_89_2_250_bib23
Wang
J. Am. Chem. Soc. , 2011
25.
High-Precision Catalysts:  Regioselective Hydroformylation of Internal Alkenes by Encapsulated Rhodium Complexes
Kuil M., Soltner T., van Leeuwen P.W., Reek J.N.
Journal of the American Chemical Society , 2006
26.
Catalytic Scaffolding Ligands: An Efficient Strategy for Directing Reactions
Lightburn T.E., Dombrowski M.T., Tan K.L.
Journal of the American Chemical Society , 2008
28.
rcr_89_2_250_bib28
Sun
J. Am. Chem. Soc. , 2010
29.
Methoxycarbonylation of styrene to methyl arylpropanoates catalyzed by palladium(II) precursors with 1,1′-bis(diphenylphosphino)metallocenes
Bianchini C., Meli A., Oberhauser W., Parisel S., Gusev O.V., Kal'sin A.M., Vologdin N.V., Dolgushin F.M.
Journal of Molecular Catalysis A Chemical , 2004
30.
rcr_89_2_250_bib30
Ionescu
2006
31.
Hydroxycarbonylation of styrene with palladium catalysts
del Rı́o I., Ruiz N., Claver C., van der Veen L.A., van Leeuwen P.W.
Journal of Molecular Catalysis A Chemical , 2000
32.
Palladium(II) complexes of new bulky bidentate phosphanes: active and highly regioselective catalysts for the hydroxycarbonylation of styrene.
Frew J.J., Damian K., Van Rensburg H., Slawin A.M., Tooze R. ., Clarke M.
Chemistry - A European Journal , 2009
33.
The scope and mechanism of palladium-catalysed Markovnikov alkoxycarbonylation of alkenes
Li H., Dong K., Jiao H., Neumann H., Jackstell R., Beller M.
Nature Chemistry , 2016
34.
Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations
Huang Z., Cheng Y., Chen X., Wang H., Du C., Li Y.
Chemical Communications , 2018
37.
Ligand-Controlled Palladium-Catalyzed Alkoxycarbonylation of Allenes: Regioselective Synthesis of α,β- and β,γ-Unsaturated Esters
Liu J., Liu Q., Franke R., Jackstell R., Beller M.
Journal of the American Chemical Society , 2015
38.
rcr_89_2_250_bib38
Ojima
1998
39.
rcr_89_2_250_bib39
Marciniec
2009
42.
The Addition of Silicon Hydrides to Olefinic Double Bonds. Part II. The Use of Group VIII Metal Catalysts
Speier J.L., Webster J.A., Barnes G.H.
Journal of the American Chemical Society , 1957
43.
rcr_89_2_250_bib43
1958
44.
rcr_89_2_250_bib44
1973
45.
rcr_89_2_250_bib45
Green
1977
47.
Photoactivated hydrosilylation reaction of alkynes
Wang F., Neckers D.C.
Journal of Organometallic Chemistry , 2003
49.
rcr_89_2_250_bib49
McLaughlin
Chem. Commun. , 2011
52.
rcr_89_2_250_bib52
Okamoto
2002
53.
The activity of Pt/SiO2 catalysts obtained by the sol-gel method in the hydrosilylation of 1-alkynes
Jiménez R., Martínez-Rosales J.M., Cervantes J.
Canadian Journal of Chemistry , 2003
54.
Hydrosilylation of alkynes catalysed by platinum on titania
Alonso F., Buitrago R., Moglie Y., Ruiz-Martínez J., Sepúlveda-Escribano A., Yus M.
Journal of Organometallic Chemistry , 2011
55.
rcr_89_2_250_bib55
Fernández
Chemistry Select , 2018
57.
Hydrosilylation of Alkenes with Early Main-Group Metal Catalysts
Buch F., Brettar J., Harder S.
Angewandte Chemie - International Edition , 2006
59.
Organometallic compounds of the lanthanides
Schumann H., Keitsch M.R., Demtschuk J., Molander G.A.
Journal of Organometallic Chemistry , 1999
65.
rcr_89_2_250_bib65
Motoda
2002
67.
Hydrosilylation of Internal Alkynes Catalyzed by Tris‐ Imidazolium Salt‐Stabilized Palladium Nanoparticles
Planellas M., Guo W., Alonso F., Yus M., Shafir A., Pleixats R., Parella T.
Advanced Synthesis and Catalysis , 2014
71.
Alkyne hydrosilylation catalyzed by nickel complexes of N-heterocyclic carbenes
73.
Regio- and Stereoselective Hydrosilylation of Unsymmetrical Alkynes Catalyzed by a Well-Defined, Low-Valent Cobalt Catalyst
Rivera-Hernández A., Fallon B.J., Ventre S., Simon C., Tremblay M., Gontard G., Derat E., Amatore M., Aubert C., Petit M.
Organic Letters , 2016
75.
Iron Catalysts for Selective Anti-Markovnikov Alkene Hydrosilylation Using Tertiary Silanes
Tondreau A.M., Atienza C.C., Weller K.J., Nye S.A., Lewis K.M., Delis J.G., Chirik P.J.
Science , 2012
76.
Iron-Catalyzed Highly Enantioselective Hydrosilylation of Unactivated Terminal Alkenes
Cheng B., Liu W., Lu Z.
Journal of the American Chemical Society , 2018
77.
Iron-Catalysed Hydrofunctionalisation of Alkenes and Alkynes
Greenhalgh M.D., Jones A.S., Thomas S.P.
ChemCatChem , 2014
79.
Dicobalt Octacarbonyl as a Catalyst for Hydrosilation of Olefins
Harrod J.F., Chalk A.J.
Journal of the American Chemical Society , 1965
82.
The cobalt(II) complex of a new tridentate Schiff-base ligand as a catalyst for hydrosilylation of olefins
Gorczyński A., Zaranek M., Witomska S., Bocian A., Stefankiewicz A.R., Kubicki M., Patroniak V., Pawluć P.
Catalysis Communications , 2016
84.
Base-Metal-Catalyzed Regiodivergent Alkene Hydrosilylations
Du X., Zhang Y., Peng D., Huang Z.
Angewandte Chemie - International Edition , 2016
87.
rcr_89_2_250_bib87
Tamura
J. Am. Chem. Soc. , 2003
90.
Asymmetric Hydrosilylation of Styrenes Catalyzed by Palladium−MOP Complexes:  Ligand Modification and Mechanistic Studies
Hayashi T., Hirate S., Kitayama K., Tsuji H., Torii A., Uozumi Y.
Journal of Organic Chemistry , 2001
91.
rcr_89_2_250_bib91
Kitayama
1995
92.
Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles
Gribble M.W., Pirnot M.T., Bandar J.S., Liu R.Y., Buchwald S.L.
Journal of the American Chemical Society , 2017
93.
Ligands with 1,10-phenanthroline scaffold for highly regioselective iron-catalyzed alkene hydrosilylation
Hu M., He Q., Fan S., Wang Z., Liu L., Mu Y., Peng Q., Zhu S.
Nature Communications , 2018
94.
rcr_89_2_250_bib94
Hiyama
1991
95.
Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds
97.
rcr_89_2_250_bib97
Tanke
1990
100.
rcr_89_2_250_bib100
Wu
2003
105.
Hydrosilylation of 1-hexyne promoted by acetone solvated gold atoms derived catalysts
Caporusso A.M., Aronica L.A., Schiavi E., Gianmario Martra, Vitulli G., Salvadori P.
Journal of Organometallic Chemistry , 2005
106.
Gold nanoparticles and gold(III) complexes as general and selective hydrosilylation catalysts.
Corma A., González-Arellano C., Iglesias M., Sánchez F.
Angewandte Chemie - International Edition , 2007
108.
Solvated gold atoms in the preparation of efficient supported catalysts: Correlation between morphological features and catalytic activity in the hydrosilylation of 1-hexyne
Aronica L.A., Schiavi E., Evangelisti C., Caporusso A.M., Salvadori P., Vitulli G., Bertinetti L., Martra G.
Journal of Catalysis , 2009
110.
Selective hydrosilylation of alkynes with a nanoporous gold catalyst
Ishikawa Y., Yamamoto Y., Asao N.
Catalysis Science and Technology , 2013
111.
rcr_89_2_250_bib111
Guo
Angew. Chem., Int. Ed. , 2016
112.
rcr_89_2_250_bib112
Ma
J. Org. Chem. , 2018
114.
rcr_89_2_250_bib114
Mo
J. Am. Chem. Soc. , 2014
115.
Asymmetric Synthesis of 1-Aryl-1,2-ethanediols from Arylacetylenes by Palladium-Catalyzed Asymmetric Hydrosilylation as a Key Step
Shimada T., Mukaide K., Shinohara A., Han J.W., Hayashi T.
Journal of the American Chemical Society , 2002
118.
Hydrosilylation of Alkynes with a Cationic Rhodium Species Formed in an Anionic Micellar System
120.
rcr_89_2_250_bib120
Ding
J. Am. Chem. Soc. , 2013
121.
Regiodivergent and Stereoselective Hydrosilylation of 1,3-Disubstituted Allenes
Miller Z.D., Dorel R., Montgomery J.
Angewandte Chemie - International Edition , 2015
127.
Catalytic Hydroboration with Rhodium Complexes
Männig D., Nöth H.
Angewandte Chemie - International Edition , 1985
128.
True Metal-Catalyzed Hydroboration with Titanium
He X., Hartwig J.F.
Journal of the American Chemical Society , 1996
132.
Nickel Catalyzed Hydroboration with Catecholborane
Kabalka G.W., Narayana C., Reddy N.K.
Synthetic Communications , 1994
133.
Ruthenium-catalyzed hydroborations of alkenes
Burgess K., Jaspars M.
Organometallics , 1993
134.
rcr_89_2_250_bib134
Luna
J. Am. Chem. Soc. , 2002
136.
Organolanthanide-Catalyzed Cyclization/Boration of 1,5- and 1,6-Dienes
138.
rcr_89_2_250_bib138
Yamamoto
Tetrahedron , 2004
139.
Ligand-Controlled Regiodivergent Cu-Catalyzed Aminoboration of Unactivated Terminal Alkenes
Sakae R., Hirano K., Miura M.
Journal of the American Chemical Society , 2015
140.
rcr_89_2_250_bib140
Su
Angew. Chem., Int. Ed. , 2015
141.
Transition-Metal-Promoted Hydroboration of Alkenes:  A Unique Reversal of Regioselectivity
Morrill T.C., D'Souza C.A., Yang L., Sampognaro A.J.
Journal of Organic Chemistry , 2002
143.
Enantioselective hydroboration mediated by homochiral rhodium catalysts
Burgess K., Ohlmeyer M.J.
Journal of Organic Chemistry , 1988
145.
Catalytic asymmetric hydroboration of styrenes
Hayashi T., Matsumoto Y., Ito Y.
Journal of the American Chemical Society , 1989
147.
Catalytic Enantioselective Hydroboration of Cyclopropenes
Rubina M., Rubin M., Gevorgyan V.
Journal of the American Chemical Society , 2003
148.
rcr_89_2_250_bib148
Chen
1999
150.
Regio- and Enantiocontrol in the Room-Temperature Hydroboration of Vinyl Arenes with Pinacol Borane
Crudden C.M., Hleba Y.B., Chen A.C.
Journal of the American Chemical Society , 2004
151.
rcr_89_2_250_bib151
Maeda
2002
152.
Hydroboration. XXII. The Reaction of Unsaturated Esters with Diborane and Disiamylborane
Brown H.C., Keblys K.A.
Journal of the American Chemical Society , 1964
154.
rcr_89_2_250_bib154
Boldrini
1990
156.
Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration
Gao T., Zhang W., Sun X., Lu H., Li B.
Journal of the American Chemical Society , 2019
157.
Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes
Smith J.R., Collins B.S., Hesse M.J., Graham M.A., Myers E.L., Aggarwal V.K.
Journal of the American Chemical Society , 2017
159.
Iron-Catalyzed 1,4-Addition of α-Olefins to Dienes
Moreau B., Wu J.Y., Ritter T.
Organic Letters , 2008
160.
Highly Selective Bis(imino)pyridine Iron-Catalyzed Alkene Hydroboration
162.
A Cobalt-Catalyzed Alkene Hydroboration with Pinacolborane
Zhang L., Zuo Z., Leng X., Huang Z.
Angewandte Chemie - International Edition , 2014
165.
rcr_89_2_250_bib165
Zhang
J. Am. Chem. Soc. , 2014
166.
Asymmetric cobalt catalysts for hydroboration of 1,1-disubstituted alkenes
Chen J., Xi T., Ren X., Cheng B., Guo J., Lu Z.
Organic Chemistry Frontiers , 2014
168.
Iron-Catalyzed, Atom-Economical, Chemo- and Regioselective Alkene Hydroboration with Pinacolborane
Zhang L., Peng D., Leng X., Huang Z.
Angewandte Chemie - International Edition , 2013
173.
Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence
174.
Efficient Homogeneous Catalysis in the Reduction of CO2 to CO
Laitar D.S., Müller P., Sadighi J.P.
Journal of the American Chemical Society , 2005
175.
Copper(I) β-Boroalkyls from Alkene Insertion:  Isolation and Rearrangement
Laitar D.S., Tsui E.Y., Sadighi J.P.
Organometallics , 2006
177.
XBphos-Rh: a halogen-bond assembled supramolecular catalyst
Carreras L., Serrano-Torné M., van Leeuwen P.W., Vidal-Ferran A.
Chemical Science , 2018
178.
Ruthenium Catalyzed Hydroboration of Terminal Alkynes to Z-Vinylboronates
Gunanathan C., Hölscher M., Pan F., Leitner W.
Journal of the American Chemical Society , 2012
180.
rcr_89_2_250_bib180
Leyva
2009
181.
Stable, Yet Highly Reactive Nonclassical Iron(II) Polyhydride Pincer Complexes: Z-Selective Dimerization and Hydroboration of Terminal Alkynes
Gorgas N., Alves L.G., Stöger B., Martins A.M., Veiros L.F., Kirchner K.
Journal of the American Chemical Society , 2017
182.
Cobalt Catalyzed Z-Selective Hydroboration of Terminal Alkynes and Elucidation of the Origin of Selectivity
Obligacion J.V., Neely J.M., Yazdani A.N., Pappas I., Chirik P.J.
Journal of the American Chemical Society , 2015
186.
rcr_89_2_250_bib186
Ramírez
2005
188.
AgSbF6-Catalyzed anti-Markovnikov hydroboration of terminal alkynes
Mamidala R., Pandey V.K., Rit A.
Chemical Communications , 2019
189.
Silver-Catalyzed Highly Regioselective Formal Hydroboration of Alkynes
Yoshida H., Kageyuki I., Takaki K.
Organic Letters , 2014
191.
Regioselective transformation of alkynes catalyzed by a copper hydride or boryl copper species
Fujihara T., Semba K., Terao J., Tsuji Y.
Catalysis Science and Technology , 2014
193.
Polyhedral Cu2 O Crystals for Diverse Aryl Alkyne Hydroboration Reactions
Tsai H., Madasu M., Huang M.H.
Chemistry - A European Journal , 2018
194.
Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates
He T., Li B., Liu L., Wang J., Ma W., Li G., Zhang Q., He W.
Chemistry - A European Journal , 2018
198.
Highly Selective Copper-Catalyzed Hydroboration of Allenes and 1,3-Dienes
Semba K., Shinomiya M., Fujihara T., Terao J., Tsuji Y.
Chemistry - A European Journal , 2013
200.
rcr_89_2_250_bib200
Gibson
2003
201.
rcr_89_2_250_bib201
Wu
J. Am. Chem. Soc. , 2009
202.
Copper(I)-Catalyzed Asymmetric Monoborylation of 1,3-Dienes: Synthesis of Enantioenriched Cyclic Homoallyl- and Allylboronates
203.
Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes
Duvvuri K., Dewese K.R., Parsutkar M.M., Jing S.M., Mehta M.M., Gallucci J.C., RajanBabu T.V.
Journal of the American Chemical Society , 2019