Palladium in Heterocyclic Chemistry (b) E.-I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis) Science of Synthesis: Cross Coupling and Heck-Type Reactions, Vols, Chem. Rev, vol.111, issue.2, pp.1170-1214, 2000. ,
, Doucet ChemCatChem, vol.2017, issue.9, pp.2895-2913, 2013.
Aryl???Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction, Chemical Reviews, vol.102, issue.5, pp.1359-1470, 2002. ,
DOI : 10.1021/cr000664r
Organosulfur Compounds: Electrophilic Reagents in Transition-Metal-Catalyzed Carbon-Carbon Bond-Forming Reactions, Angewandte Chemie International Edition, vol.37, issue.47, pp.7674-7684, 2005. ,
DOI : 10.1246/nikkashi.1987.2148
Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2011. ,
, Rev, vol.42, pp.599-621, 2013.
, J. Chem. Soc, issue.5, pp.1307-1311, 1955.
, , pp.877-878, 1974.
(d) S. Fujita, Synthesis, pp.445-452, 1979. ,
, J. Org. Chem, vol.53, pp.2047-2052, 1988.
, , pp.1499-1501, 2003.
Copper-catalyzed additions of sulfonyl iodides to simple and cyclic alkenes, The Journal of Organic Chemistry, vol.45, issue.3, pp.406-410, 1980. ,
DOI : 10.1021/jo01291a006
, Chem. Commun, vol.14, issue.51, pp.3436-3440, 2012.
, Org. Biomol. Chem, vol.2012, issue.16, pp.7479-7482, 2014.
, , pp.978-991, 2015.
Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes, Journal of the American Chemical Society, vol.125, issue.50, pp.15292-15293, 2003. ,
DOI : 10.1021/ja038328q
, Synlett, issue.10, pp.1235-1238, 2004.
, Chem. Commun, issue.11, pp.866-867, 1979.
, , pp.95-98, 2004.
, , pp.1891-1894, 2006.
, , pp.57923-57928, 2014.
, , pp.27029-27033, 2015.
Desulfonative pd-catalyzed coupling of aryl trifluoroborates with arylsulfonyl chlorides, Applied Organometallic Chemistry, vol.5, issue.9, pp.767-771, 2016. ,
DOI : 10.1039/C5RA01363A
,
, , 2018.
Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate, The Journal of Organic Chemistry, vol.53, issue.4, pp.918-920, 1988. ,
DOI : 10.1021/jo00239a056
Palladium-Catalyzed Hiyama-Type Cross-Coupling Reactions of Arenesulfinates with Organosilanes, The Journal of Organic Chemistry, vol.78, issue.10, pp.5022-5025, 2013. ,
DOI : 10.1021/jo302791q
Pd-catalyzed desulfitative Hiyama coupling with sulfonyl chlorides, Applied Organometallic Chemistry, vol.78, issue.5, pp.379-381, 2014. ,
DOI : 10.1021/jo302791q
Palladium-catalyzed Hiyama coupling reaction of arylsulfonyl hydrazides under oxygen, Organic & Biomolecular Chemistry, vol.11, issue.16, pp.4647-4651, 2015. ,
DOI : 10.1039/c3ob40518d
Palladium-Catalyzed Desulfitative Arylation by C???O Bond Cleavage of Aryl Triflates with Sodium Arylsulfinates, The Journal of Organic Chemistry, vol.77, issue.22, pp.10468-10472, 2012. ,
DOI : 10.1021/jo302005s
Palladium-Catalyzed Desulfitative Cross-Coupling of Sodium Arylsulfinates with Aryl Bromides and Chlorides: An Alternative Convenient Synthesis of Biaryls, Chinese Journal of Chemistry, vol.33, issue.10, pp.1269-1273, 2013. ,
DOI : 10.1021/ar980063a
, , pp.1715-1721, 2013.
, , pp.1520-1523, 2013.
)-furanone with Sodium Arylsulfinates, European Journal of Organic Chemistry, vol.52, issue.6, pp.1193-1197 ,
DOI : 10.1021/ie401149p
An efficient tandem elimination???cyclization???desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates, Org. Biomol. Chem., vol.68, issue.3, pp.420-424, 2013. ,
DOI : 10.1021/jo0349835
, Chem. Lett, issue.27, pp.459-460, 1990.
, , pp.7125-7128, 2005.
-Catalyzed Desulfonylative Homocoupling of Arylsulfonyl Chlorides, Chinese Journal of Chemistry, vol.13, issue.5, pp.535-538, 2015. ,
DOI : 10.1021/ol102688e
, , pp.3436-3440, 2012.
, J. Chem. Res, vol.2016, issue.41, pp.1-3
The homocoupling of arylsulfonylhydrazides by palladium-catalysed desulfonation in air, Journal of Chemical Research, vol.37, issue.11, pp.674-676, 2013. ,
DOI : 10.3184/174751913X13813357379921
Aryl???Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation, Chemical Reviews, vol.107, issue.1, pp.174-238, 2007. ,
DOI : 10.1021/cr0509760
Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C???H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates, Tetrahedron, vol.65, issue.50, pp.10269-10310, 2009. ,
DOI : 10.1016/j.tet.2009.10.015
, Angew. Chem. Int. Ed, vol.48, pp.9792-9826, 2009.
, Yu Angew. Chem. Int. Ed, vol.48, pp.5094-5115, 2009.
, Coord. Chem. Rev. Catal. Sci. Technol, vol.254, issue.1, pp.456-469, 2010.
, Angew. Chem. Int. Ed. Chem. Rev, vol.51, issue.112, pp.10236-10254, 2012.
, Catal. Sci. Technol, vol.2013, issue.3, pp.562-571
, Chem. Sci. 2013 Adv. Synth. Catal, vol.5, issue.356, pp.369-375, 2013.
, ChemCatChem, vol.2014, issue.6, pp.1824-1859
, Tetrahedron, vol.2016, issue.72, pp.1795-1837
, Cat. Sci. Technol. 2016, vol.6, 2005.
, Chem. Asian J, vol.13, pp.143-157, 2018.
Palladium-Catalyzed Desulfitative Direct C???H Arylation of Electron-Deficient Polyfluoroarenes with Sodium Arenesulfinates, Advanced Synthesis & Catalysis, vol.117, issue.2-3, pp.429-436, 2014. ,
DOI : 10.1016/S0022-1139(02)00157-4
, , pp.76-80, 2014.
, Tetrahedron, vol.2017, issue.73, pp.5337-5343
Palladium-Catalyzed Direct and Site-Selective Desulfitative Arylation of Indoles with Sodium Sulfinates, Advanced Synthesis & Catalysis, vol.140, issue.2-3, pp.335-340, 2012. ,
DOI : 10.1016/j.cattod.2008.07.013
Microwave-Accelerated Pd-Catalyzed Desulfitative Direct C2-Arylation of Free (NH)-Indoles with Arylsulfinic Acids, Chemistry - An Asian Journal, vol.52, issue.12, pp.3185-3190, 2013. ,
DOI : 10.1016/j.tetlet.2011.08.075
Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners, Advanced Synthesis & Catalysis, vol.4, issue.18, pp.3831-3841, 2014. ,
DOI : 10.1039/c3sc51206a
URL : https://hal.archives-ouvertes.fr/hal-01114553
, Tetrahedron, vol.2015, issue.39, p.71
, , pp.65175-65183, 2015.
Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzenesulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls, European Journal of Organic Chemistry, vol.24, issue.20, pp.4428-4436 ,
DOI : 10.1055/s-0032-1318155
, , pp.3544-3554, 2015.
, , pp.1794-1804, 2015.
Desulfitative palladium-catalyzed direct C-3 arylation of indolizines with arylsulfonyl chlorides, Applied Organometallic Chemistry, vol.78, issue.8, pp.524-527 ,
DOI : 10.1021/jo302791q
, , pp.21814-21821, 2016.
Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners, Advanced Synthesis & Catalysis, vol.4, issue.18, pp.3831-3841, 2014. ,
DOI : 10.1039/c3sc51206a
URL : https://hal.archives-ouvertes.fr/hal-01114553
Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides, Organic & Biomolecular Chemistry, vol.351, issue.21, pp.4947-4956, 2016. ,
DOI : 10.1002/adsc.200900004
URL : https://hal.archives-ouvertes.fr/hal-01341571
Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides, Organic & Biomolecular Chemistry, vol.127, issue.10, pp.2824-2827, 2016. ,
DOI : 10.1021/ja043273t
, Chem. Sci, vol.2014, issue.5, pp.392-396
)???H bond arylations, Beilstein Journal of Organic Chemistry, vol.11, issue.49, pp.2012-2020, 2015. ,
DOI : 10.3762/bjoc.11.218
, , pp.4182-4185, 2016.
, , pp.2515-2523, 2014.
, ChemCatChem, vol.2014, issue.6, pp.1303-1309
Modulating Reactivity and Diverting Selectivity in Palladium-Catalyzed Heteroaromatic Direct Arylation Through the Use of a Chloride Activating/Blocking Group, The Journal of Organic Chemistry, vol.75, issue.4, pp.1047-1060, 2010. ,
DOI : 10.1021/jo902515z
Unprecedented Access to ??-Arylated Selenophenes through Palladium-Catalysed Direct Arylation, Chemistry - A European Journal, vol.138, issue.12, pp.2788-2791, 2017. ,
DOI : 10.1021/jacs.5b12242
URL : https://hal.archives-ouvertes.fr/hal-01501260
Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C???H bond with arene sulfonyl chlorides, Chemical Communications, vol.132, issue.41, pp.11522-11524, 2011. ,
DOI : 10.1021/ja101939r
, Tetrahedron, vol.2012, issue.68, 1926.
, Org. Biomol. Chem, vol.2017, issue.15, pp.8504-8507
, Org. Biomol. Chem, vol.2012, issue.10, pp.7479-7482
, , pp.2714-2718, 2012.
Palladium-catalyzed desulfitative C???H arylation of azoles with sodium sulfinates, Organic & Biomolecular Chemistry, vol.47, issue.22, pp.7675-7679, 2011. ,
DOI : 10.1039/c1cs15093f
Palladium-Catalyzed Desulfitative C???H Arylation of Heteroarenes with Sodium Sulfinates, Chemistry - A European Journal, vol.132, issue.48, pp.13415-13419, 2011. ,
DOI : 10.1021/ja1045378
Palladium-Catalyzed Direct Arylation of N-Heteroarenes with Arylsulfonyl Hydrazides, Chemistry - A European Journal, vol.14, issue.35, pp.10830-10833, 2012. ,
DOI : 10.1021/ol300348w
, , pp.586-590, 2014.
, , pp.1124-1130, 2015.
de Vries Can The Mizoroki?Heck Reaction, J. Chem. Chem. Soc. Rev, vol.79, issue.23, pp.1086-1092, 2001. ,
, , pp.975-976, 1989.
, J. Chem. Soc. Perkin trans, vol.1, issue.66, pp.2207-2211, 1990.
, , pp.3097-3106, 2016.
Palladium-Catalyzed Desulfitative Mizoroki-Heck Couplings of Sulfonyl Chlorides with Mono- and Disubstituted Olefins: Rhodium-Catalyzed Desulfitative Heck-Type Reactions under Phosphine- and Base-Free Conditions, Chemistry - A European Journal, vol.68, issue.9, pp.2633-2641, 2005. ,
DOI : 10.1246/nikkashi.1987.2148
, , pp.1432-1435, 2011.
Pd-catalyzed ligand-free desulfitative Heck reaction with arenesulfinic acid salts under air, Applied Organometallic Chemistry, vol.47, issue.3, pp.188-190, 2013. ,
DOI : 10.1039/c1cc13352g
, Synlett, vol.2013, issue.71, pp.2571-2574
Oxidative Mizoroki-Heck-Type Reaction of Arylsulfonyl Hydrazides for a Highly Regio- and Stereoselective Synthesis of Polysubstituted Alkenes, Chemistry - A European Journal, vol.39, issue.6, pp.1582-1585, 2012. ,
DOI : 10.1039/b902868d
, , pp.27584-27589, 2016.
Palladium-Catalyzed Desulfitative Heck-Type Reaction of Aryl Sulfinic Acids with Alkenes, Chemistry - A European Journal, vol.3, issue.21, pp.5787-5790, 2011. ,
DOI : 10.1021/ol016529y
Palladium-Catalyzed Desulfitative Oxidative Coupling between Arenesulfinic Acid Salts and Allylic Alcohols: A Strategy for the Selective Construction of ??-Aryl Ketones and Aldehydes, The Journal of Organic Chemistry, vol.80, issue.17, pp.8903-8909, 2015. ,
DOI : 10.1021/acs.joc.5b01463
-Arylation of Glycals by Using Benzenesulfonyl Chlorides, European Journal of Organic Chemistry, vol.11, issue.3, pp.459-462 ,
DOI : 10.1021/ol900273d
-Glycosylation of Glycals with Sodium Arylsulfinates, European Journal of Organic Chemistry, vol.10, issue.5, pp.949-952 ,
DOI : 10.3390/10080859
Palladium-Catalyzed Desulfitative Conjugate Addition of Aryl Sulfinic Acids and Direct ESI-MS for Mechanistic Studies, The Journal of Organic Chemistry, vol.77, issue.10, pp.4849-4853, 2012. ,
DOI : 10.1021/jo300654s
, , pp.4347-4350, 2012.
, Synthesis, vol.2013, issue.45, pp.2867-2874
, Sci. Technol, vol.5, pp.2904-2912, 2015.
, J. Org. Chem. Org. Chem. Front, vol.2016, issue.4, pp.4744-4750, 1921.
, , pp.8121-8126, 2016.
Palladium-Catalyzed Oxidative Heck-Type Alkylation/Aryl Migration/Desulfonylation between Alkenes with ??-Carbonyl Alkyl Bromides, Organic Letters, vol.17, issue.4, pp.836-539, 2015. ,
DOI : 10.1021/ol503660a
Palladium-catalyzed desulfitative hydroarylation of alkynes with sodium sulfinates, Chemical Communications, vol.43, issue.68, pp.7501-7503, 2013. ,
DOI : 10.1002/anie.200460409
Palladium-Catalyzed Cross-Coupling Reaction of Sodium Sulfinates with Alkynes, Advanced Synthesis & Catalysis, vol.54, issue.9, pp.2029-2039, 2014. ,
DOI : 10.1021/jo00272a002
Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes, The Journal of Organic Chemistry, vol.82, issue.13, pp.6764-6769, 2017. ,
DOI : 10.1021/acs.joc.7b00899
Direct Synthesis of Aryl Ketones by Palladium-Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles, Chemistry - A European Journal, vol.13, issue.29, pp.7996-7999, 2011. ,
DOI : 10.1021/ol200101x
Synthesis of ketones by palladium-catalysed desulfitative reaction of arylsulfinic acids with nitriles, Chemical Communications, vol.17, issue.33, pp.9501-9503, 2011. ,
DOI : 10.1002/chem.201100539
, , pp.1455-1459, 2011.
,
, J. Org. Chem, vol.2014, issue.79, pp.12018-12032
, Chem. Commun, vol.2012, issue.48, pp.499-451
, Org. Biomol. Chem, vol.2014, issue.12, pp.4078-4083
, Acknowledgements We thank China Scholarship Council for providing financial support to H. L.; CEFIPRA for providing financial support to A. S.; and ANR for providing financial support to X. S. Bibliographical sketch
He joined the international master's program " Catalysis, Molecules and Green Chemistry " in the University of Rennes 1 (France) in 2015. He performed his master's research training in Prof. C. Darcel's team in the University of Rennes 1. He currently works towards a PhD degree of ENSCR under the supervision of Dr, Henri Doucet. He received a grant from the China Scholarship Council (CSC) in 2017. His work focuses on the C-H bond functionalization using palladium catalysis ,
Sc degree in Chemistry from University of Calcutta in 2014 He received his M.Sc degree in Chemistry from IIT Madras in 2016, Afterwards, he did International Master in Molecular Catalysis and Green Chemistry from University of Rennes, vol.1 ,
, Now he is a PhD student at University of Rennes 1 (France) under the supervision of Prof. Henri Doucet and Dr
She joined the international master's program " Catalysis, Molecules and Green Chemistry " in the University of Rennes 1 (France) receiving grants from the Foundation Rennes 1 in 2015. She performed her master's research training in H. Doucet's team ,
, She currently works towards a PhD degree of University of Rennes 1 under the supervision of Dr
Jean-François Soulé. Her work focuses on the C-H bond functionalization using palladium catalysis ,
Soulé completed his PhD in 2007 working on the Petasis reaction applied on the synthesis of biological interest molecules under the supervision of the Prof ,
, Gif-sur-Yvette (France) In 2010, he joined the group of the Prof Shu Kobayashi at the University of Tokyo (Japan) as a postdoctoral fellow, Institut de Chimie des Substances Naturelles he was appointed as " Chargé de Recherche " CNRS at the University of Rennes 1 in the group of Dr. Henri Doucet. His main interest focuses on the development of sustainable chemistry, notably, transition-metals catalyzed C-H functionalizations, 2013.
, After post-doctoral appointments at Oxford university (UK) with Prof His research interests include organic synthesis by metal-catalyzed processes, ligands synthesis and green chemistry, Henri Doucet received his PhD in chemistry working withJapan) with Prof. R. Noyori, he moved to the University of Marseille (France) as CNRS researcher in the group of Prof M. Santelli. In 2006 he moved to Rennes 1 University, 1994.