Publications

2016 -

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: https://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://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