Publications

2021-

Stereospecific indium(III)-catalysed tandem cycloisomerization of functionalized 1,6-enynes: scope and mechanistic insights

Raquel Pérez-Guevara, Luis A. Sarandeses, Rosana Álvarez, M. Montserrat Martínez  and José Pérez Sestelo

Adv. Synth. Cat. 2024, doi.org/10.1002/adsc.202301329

Abstract
Indium organometallics in transition metal-catalyzed cross-coupling reactions

M. Montserrat Martínez, Jose Perez Sestelo, and Luis A. Sarandeses

Advances in Organometallic Chemistry 2023, vol 80, pp  177-253 (10.1016/bs.adomc.2023.02.001)

Abstract
Synthesis of 1H-Isochromenes and 1,2-Dihydroisoquinolines by Indium(III)-Catalyzed Cycloisomerization of ortho-(Alkynyl)benzyl Derivatives

Fabio Seoane-Carabel, Lorena Alonso-Marañón, Luis A. Sarandeses, José Pérez Sestelo

Synthesis 2023, 55,  1714-1723 (10.1055/s-0042-1751383)

Abstract
Indium-catalyzed synthesis of benzannulated spiroketals by intramolecular double hydroalkoxylation of ortho-(hydroxyalkynyl)benzyl alcohols

Raquel Pérez-Guevara, Luis A. Sarandeses, M. Montserrat Martínez and José Pérez Sestelo

Org. Chem. Front., 2022, 9, 6894 (DOI: 10.1039/d2qo01600a)

Abstract
Microwave-assisted direct synthesis of BODIPY dyes and derivatives

Ana Da Lama, José Pérez Sestelo, Luis A. Sarandeses and M. Montserrat Martínez

Org. Biomol. Chem., 2022, 20, 9132–9137 DOI: https://doi.org/10.1039/d2ob01349e

Abstract
Synthesis and structural analysis of push-pull imidazole-triazole based fluorescent bifunctional chemosensor for Cu2+ and Fe2+ detection

Ana Da Lama, José Pérez Sestelo, Laura Valencia, David Esteban-Gómez, Luis
A. Sarandeses, M. Montserrat Martínez

Dyes and Pigments 205 (2022) 110539, DOI: 10.1016/j.dyepig.2022.110539

Abstract
New Insights into the Exploitation of BODIPY Derivatives as Organic Photocatalyst

Ana Da Lama, Beatrice Bartolomei, Cristian Rosso, Giacomo Filippini,
M. Montserrat Martínez, Luis A. Sarandeses, and Maurizio Prato

Eur. J. Org. Chem. 2022, e202200622, doi: 10.1002/ejoc.202200622

Abstract
Merging Iridium-Catalyzed C–H Borylations with Palladium-Catalyzed Cross-Couplings using Triorganoindium Reagents

Chathurika R. K. Jayasundara, José M. Gil-Negrete, Jose R. Montero Bastidas, M. Montserrat Martínez, José Pérez Sestelo, Milton R. Smith, III, Robert E. Maleczka, Jr.

J. Org. Chem. 2022, 87, 751−759, DOI: 10.1021/acs.joc.1c01978

Abstract
Indium(III)-catalyzed stereoselective synthesis of tricyclic frameworks by cascade cycloisomerization reactions of aryl 1,5-enynes

Ramón E. Millán, Jaime Rodríguez, Luis A. Sarandeses, Enrique Gómez-Bengoa, and José Pérez Sestelo

J. Org. Chem. 2021, 86, 10.1021/acs.joc.1c00825

Abstract

2016-2020

Advances in Cross-Coupling Reactions

José Pérez Sestelo and Luis A. Sarandeses

Molecules 2020, 25, 4500; doi:10.3390/molecules25194500

Abstract
Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

Gil-Negrete, J. M.; Pérez Sestelo, J.; Sarandeses, L. A.

J. Org. Chem. 2019, 84, 9778-9785. DOI: doi.org/10.1021/acs.joc.9b00928

Abstract
Synthesis of D-A-A and D-A-D Pyrimidine π-Systems Using Triorganoindium Reagents: Optical, Vibrational and Electrochemical Studies

Pérez-Caaveiro, C.; Moreno Oliva, M.; López Navarrete, J. T.; Pérez Sestelo, J.; Martínez, M. M.; Sarandeses, L. A.

 

J. Org. Chem. 2019, 84, 8870-8885. DOI: http://doi.org/10.1021/acs.joc.9b00643

Abstract
Indium(III) as π-acid catalyst for the electrophilic activation of carbon–carbon unsaturated systems.

Pérez Sestelo, J. ; Sarandeses, L. A.; Martínez, M. M.; Alonso-Marañón, L.

Org. Biomol. Chem. 2018, 16, 5733–5747 (DOI: 10.1039/c8ob01426d).

Abstract
Triorganoindium reagents in Rh-catalyzed C–H activation/C–C cross-coupling reactions of 2-arylpyridines

Riveiros, R.; Tato, R.; Pérez Sestelo, J.; Sarandeses, L. A.

Molecules 2018, 23, 1582 (DOI: 10.3390/molecules23071582).

Abstract
Synthesis of fused chromenes by indium(III)-catalyzed cascade hydroarylation/cycloisomerization reactions of polyyne-type aryl propargyl ethers.

Alonso-Marañón, L.; Sarandeses, L. A.; Martínez, M. M.; Pérez Sestelo, J.

Org. Chem. Front. 2018, 5, 2308–2312 (DOI: 10.1039/c8qo00457a).

Abstract
Indium(III)-catalyzed synthesis of benzo[b]furans by intramolecular hydroalkoxylation of ortho-alkynylphenols: scope and mechanistic insights.

Alonso-Marañón, L.; Martínez, M. M.; Sarandeses, L. A.; Gómez-Bengoa, E.; Pérez Sestelo, J.

J. Org. Chem. 2018, 83, 7970–7980 (DOI: 10.1021/acs.joc.8b00829).

Abstract
Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions

Gil-Negrete, J. M.; Pérez Sestelo, J.; Sarandeses, L. A.

Chem. Commun. 2018, 54, 1453–1456 (DOI: 10.1039/c7cc09344f).

Abstract
Ferrocenylindium reagents in palladium-catalyzed cross-coupling reactions: asymmetric synthesis of planar chiral 2-aryl oxazolyl and sulfinyl ferrocenes.

Mato, M.; Pérez-Caaveiro, C.; Sarandeses, L. A.; Pérez Sestelo, J.

Adv. Synth. Catal. 2017, 359, 1388–1393 (DOI: 10.1002/adsc.201601397).

Abstract
Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines.

Alonso-Marañón, L.; Sarandeses, L. A.; Martínez, M. M.; Pérez Sestelo, J.

Org. Chem. Front. 2017, 4, 500–505 (DOI: 10.1039/C6QO00721J).

Abstract
Transition-metal-free cross-coupling of indium organometallics with chromene and isochroman acetals mediated by BF3•OEt2.

Gil-Negrete, J. M.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Lett. 2016, 18, 4316–4319 (DOI: 10.1021/acs.orglett.6b02058).

Abstract

2011-2015

Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers.

Alonso-Marañón, L.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

Org. Biomol. Chem. 2015, 13, 379–387 (DOI: 10.1039/c4ob02033b).

Highlighted in: Snieckus, V.; Maheta, A. Synfacts 2015, 11, 255 (DOI: 10.1055/s-0034-1380240).

Abstract
Nonsymmetrical 3,4-dithienylmaleimides by cross-coupling reactions using indium organometallics: synthesis and photochemical studies.

Mosquera, Á.; Férnandez, M. I.; Canle L., M.; Pérez Sestelo, J.; Sarandeses, L. A.

Chem. Eur. J. 2014, 20, 14524–14530 (DOI: 10.1002/chem.201403736).

Abstract
Triorganoindium reagents in selective palladium catalyzed cross-coupling with iodoimidazoles: synthesis of neurodazine.

Pérez-Caaveiro, C.; Pérez Sestelo, J.; Martínez, M. M.; Sarandeses, L. A.

J. Org. Chem. 2014, 79, 9586–9593 (DOI: 10.1021/jo501664p).
Highlighted in: Knochel, P.; Hammann, J. M. Synfacts 2015, 11, 75 (DOI: 10.1055/s-0034-1379660).

Abstract
Synthesis of axially chiral 1,1′-binaphthalenes by palladium-catalyzed cross-coupling reactions of triorganoindium reagents.

Mosquera, A.; Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A.

Eur. J. Org. Chem. 2013, 2555–2562 (DOI: 10.1002/ejoc.201300042).

Abstract
Organogold(I) phosphanes in palladium-catalyzed cross-coupling reactions in aqueous media.

Peña-López, M.; Sarandeses, L. A.; Pérez Sestelo, J.

Eur. J. Org. Chem. 2013, 2545–2554 (DOI: 10.1002/ejoc.201201720).

Abstract
Synthesis of 4,6-disubstituted 2-(4-morpholinyl)pyrimidines by cross-coupling reactions using triorganoindium compounds.

Martínez, M. M.; Pérez-Caaveiro, C.; Peña-López, M.; Sarandeses, L. A.; Pérez Sestelo, J.

Org. Biomol. Chem. 2012, 10, 9045–9051 (DOI: 10.1039/c2ob26398j).

Abstract
Rhodium-catalyzed allylic substitution reactions using indium(III) organometallics.

Riveiros, R.; Tato, R.; Pérez Sestelo, J.; Sarandeses, L. A.

Eur. J. Org. Chem. 2012, 3018–3023 (DOI: 10.1002/ejoc.201200104).

Abstract
Synthesis of functionalized thiophenes and oligothiophenes by selective and iterative cross-coupling reactions using indium organometallics.

Martínez, M. M.; Peña-López, M.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Biomol. Chem. 2012, 10, 3892–3898 (DOI: 10.1039/c2ob25123j).

Abstract
Palladium-catalyzed cross-coupling reactions of organogold(I) phosphanes with allylic electrophiles.

Peña-López, M.; Ayán-Varela, M.; Sarandeses, L. A.; Pérez Sestelo, J.

Org. Biomol. Chem. 2012, 10, 16861694 (DOI: 10.1039/c2ob06788a).

Abstract
Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds.

Tato, R.; Riveiros, R.; Pérez Sestelo, J.; Sarandeses, L. A.

Tetrahedron 2012, 68, 1606–1611 (DOI: 10.1016/j.tet.2011.11.075).

Abstract

2006-2010

Palladium-catalyzed cross-coupling reactions of organogold(I) reagents with organic electrophiles.

Peña-López, M.; Ayán-Varela, M.; Sarandeses, L. A.; Pérez Sestelo, J.

Chem. Eur. J. 2010, 16, 9905–9909 (DOI: 10.1002/chem.201000726).

Abstract
A versatile synthesis of fumaquinone

Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

J. Org. Chem. 2010, 75, 5337–5339 (DOI: 10.1021/jo100779z).

Abstract
A versatile enantioselective synthesis of barrenazines.

Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

Org. Lett. 2010, 12, 852–854 (DOI: 10.1021/ol902920u).

Addition/Correction: Org. Lett. 2011, 13, 4151–4151 (DOI: 10.1021/ol201592g).

Abstract
Synthesis of 3,4-disubstituted maleimides by selective cross-coupling reactions using indium organometallics.

Bouissane, L.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Lett. 2009, 11, 1285–1288 (DOI: 10.1021/ol900063p).

Abstract
Total synthesis of (+)-neomarinone.

Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

Chem. Eur. J. 2009, 15, 910–916 (DOI: 10.1002/chem.200802021).

Abstract
Cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines: synthesis of hyrtinadine A.

Mosquera, A.; Riveiros, R.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Lett. 2008, 10, 3745–3748 (DOI: 10.1021/ol801393n).

Abstract
Palladium-catalyzed cross-coupling reactions of triorganoindium reagents with alkenyl halides.

Riveiros, R.; Saya, L.; Pérez Sestelo, J.; Sarandeses, L. A

Eur. J. Org. Chem. 2008, 1959–1966 (DOI: 10.1002/ejoc.200701216).

Abstract
Enantioselective nickel-catalyzed cross-coupling reactions of trialkynylindium reagents with racemic secondary benzyl bromides.

Caeiro, J.; Pérez Sestelo, J.; Sarandeses, L. A.

Chem. Eur. J. 2008, 14, 741–746 (DOI: 10.1002/chem.200701035).

Abstract
Enantioselective synthesis of (–)-barrenazines A and B.

Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

Tetrahedron Lett. 2007, 48, 8536–8538 (DOI: 10.1016/j.tetlet.2007.09.145).

Abstract
Synthesis of allenes by palladium-catalyzed SN2′ reaction of indium organometallics with propargylic esters.

Riveiros, R.; Pérez Sestelo, J.; Sarandeses, L. A.

Synthesis 2007, 3595–3598 (DOI: 10.1055/s-2007-983849).

Abstract
Synthetic studies on neomarinone: practical and efficient stereoselective synthesis of the side chain.

Suárez, R. M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

Tetrahedron Lett. 2007, 48, 6493–6495 (DOI: 10.1016/j.tetlet.2007.07.064).

Abstract
Palladium-catalyzed aryl-aryl cross-coupling reaction using ortho-substituted arylindium reagents.

Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A.

J. Org. Chem. 2007, 72, 1271–1275 (DOI: 10.1021/jo062148s).
Highlighted in: Knochel, P.; Thaler, T. Synfacts 2007, 531 (DOI: 10.1055/s-2007-968435).

Abstract
Palladium-catalyzed cross-coupling reaction of triorganoindium reagents with propargylic esters.

Riveiros, R.; Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Lett. 2006, 8, 1403–1406 (DOI: 10.1021/ol060192o).

Abstract

2001-2005

New synthetic applications of indium organometallics in cross-coupling reactions.

Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A.

Synthesis 2005, 485–492 (DOI: 10.1055/s-2004-834945).

Abstract
Practical and efficient enantioselective synthesis of α-amino acids in aqueous media.

Suárez, R. M.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Biomol. Chem. 2004, 2, 3584–3587 (DOI: 10.1039/b413017k).

Abstract
Palladium-catalyzed cross-coupling reactions of allylic halides and acetates with indium organometallics.

Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A.

J. Org. Chem. 2004, 69, 8136–8139 (DOI: 10.1021/jo0491511).

Abstract
Stereoselective convergent synthesis of 24-substituted metabolites and analogues of vitamin D.

Cornella, I.; Suárez, R. M.; Mouriño, A.; Pérez Sestelo, J.; Sarandeses, L. A.

J. Steroid Biochem. Mol. Biol. 2004, 89-90, 19–23 (DOI: 10.1016/j.jsbmb.2004.03.045).

Abstract
Diastereoselective conjugate addition to chiral α,β-unsaturated carbonyl systems in aqueous media: an enantioselective entry to α- and γ-hydroxy acids and α-amino acids.

Suárez, R. M.; Pérez Sestelo, J.; Sarandeses, L. A.

Chem. Eur. J. 2003, 9, 4179–4187 (DOI: 10.1002/chem.200304790).

Abstract
Palladium-catalyzed carbonylative coupling reactions using triorganoindium compounds.

Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A.

Synthesis 2003, 780–784 (DOI: 10.1055/s-2003-38060).

Abstract
Copper-catalyzed regioselective allylic substitution reactions with indium organometallics.

Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A.

J. Org. Chem. 2003, 68, 2518–2520 (DOI: 10.1021/jo0265939).

Abstract
Inner-outer ring 1,3-bis(trimethylsilyloxy)-1,3-dienes as useful intermediates in the synthesis of helicenes.

Real, M. M.; Pérez Sestelo, J.; Sarandeses, L. A.

Tetrahedron Lett. 2002, 43, 9111–9114 (DOI: 10.1016/S0040-4039(02)02246-3).

Abstract
Multifold and sequential cross-coupling reactions with indium organometallics.

Pena, M. A.; Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A.

Chem. Commun. 2002, 2246–2247 (DOI: 10.1039/b206346h).

Abstract
Diastereoselective ultrasonically induced zinc-copper conjugate addition to chiral α,β-unsaturated carbonyl systems in aqueous media.

Suárez, R. M.; Pérez Sestelo, J.; Sarandeses, L. A.

Synlett 2002, 1435–1438 (DOI: 10.1055/s-2002-33604).

Abstract
Synthesis of new 18-substituted analogues of calcitriol using a photochemical remote functionalization.

Cornella, I.; Pérez Sestelo, J.; Mouriño, A.; Sarandeses, L. A.

J. Org. Chem. 2002, 67, 4707–4714 (DOI: 10.1021/jo020022z).

Abstract
Stereoselective convergent synthesis of 24,25-dihydroxyvitamin D3 metabolites: a practical approach

Pérez Sestelo, J.; Cornella, I.; de Uña, O.; Mouriño, A.; Sarandeses, L. A.

Chem. Eur. J. 2002, 8, 2747–2752 (DOI: 10.1002/1521-3765(20020617)8:12<2747::AID-CHEM2747>3.0.CO;2-J).

Abstract
Synthesis of the first 24-aminovitamin D3 derivatives by diastereoselective conjugate addition to a chiral methyleneoxazolidinone in aqueous media.

Pérez Sestelo, J.; de Uña, O.; Mouriño, A.; Sarandeses, L. A.

Synlett 2002, 719–722 (DOI: 10.1055/s-2002-25339).

Abstract
Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles.

Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A.

J. Am. Chem. Soc. 2001, 123, 4155–4160 (DOI: 10.1021/ja004195).

Abstract
Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes.

Pérez Sestelo, J.; Real, M. M.; Sarandeses, L. A.

J. Org. Chem. 2001, 66, 1395–1402 (DOI: 10.1021/jo0015319).

Abstract

-2000

Synthesis of vitamin D3 and calcitriol dimers as potential chemical inducers of vitamin D receptor dimerization.

Pérez Sestelo, J.; Mouriño, A.; Sarandeses, L. A.

J. Org. Chem. 2000, 65, 8290–8296 (DOI: 10.1021/jo001084x).

Abstract
Palladium-catalyzed cross-coupling reactions of triorganoindium compounds with vinyl and aryl triflates or iodides.

Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A.

Org. Lett. 1999, 1, 1267–1269 (DOI: 10.1021/ol990939t).

Abstract
Design and synthesis of a 1α,25-dihydroxyvitamin D3 dimer as a potential chemical inducer of vitamin D receptor dimerization

Pérez Sestelo, J.; Mouriño, A.; Sarandeses, L. A.

Org. Lett. 1999, 1, 1005–1007 (DOI: 10.1021/ol990878z).

Abstract
Synthesis of polycyclic structures by Diels-Alder reaction of inner-outer-ring 1,3-bis[(trimethylsilyl)oxy]dienes.

Pérez Sestelo, J.; Real, M. M.; Mouriño, A.; Sarandeses, L. A.

Tetrahedron Lett. 1999, 40, 985–988 (DOI: 10.1016/S0040-4039(98)02463-0).

Abstract
First nickel-catalyzed 1,4-conjugate additions to α,β-unsaturated systems using triorganoindium compounds.

Pérez, I.; Pérez Sestelo, J.; Maestro, M. A.; Mouriño, A.; Sarandeses, L. A.

J. Org. Chem. 1998, 63, 10074–10076 (DOI: 10.1021/jo981830m).

Abstract