New insight in Hiyama cross-coupling reactions: Decarboxylative, denitrogenative and desulfidative couplings

Document Type : Review Article

Authors

1 Department of Science, Payame Noor University, P. O. Box: 19395-4697 Tehran, Iran

2 Department of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, Iran

Abstract

In this mini-review, recent advances and developments in the decarboxylative, denitrogenative, and desulfidative Hiyama-type cross-coupling reaction from 2011 up present are studied. This review focused mainly on mechanistic aspects of Hiyama cross-coupling reactions

Graphical Abstract

New insight in Hiyama cross-coupling reactions: Decarboxylative, denitrogenative and desulfidative couplings

Keywords


 
References
[1] C.C. Johansson Seechurn, MO Kitching, TJ Colacot, V Snieckus, Palladium‐catalyzed cross‐coupling: a historical contextual perspective to the 2010 Nobel Prize, Angew. Chem. Int. Ed., 51 (2012) 5062-5085.
[2] I.P. Beletskaya, V.P. Ananikov, Transition-metal-catalyzed C−S, C−Se, and C−Te bond formation via cross-coupling and atom-economic addition reactions, Chem. Rev., 111 (2011) 1596-1636.
[3] H.F. Sore, W.R. Galloway, D.R. Spring, Palladium-catalysed cross-coupling of organosilicon reagents, Chem. Soc. Rev., 41 (2012) 1845-1866.
[4] F Foubelo, C Nájera, M Yus, The Hiyama cross‐coupling reaction: New discoveries, Chem Rec, 16 (2016) 2521-2533.
[5] M. Abdoli, H. Saeidian, Synthesis and reactivity of imidazole-1-sulfonate esters (imidazylates) in substitution, elimination, and metal-catalyzed cross-coupling reactions: a review, J. Sulfur. Chem., 36 (2015) 556-582.
[6] S. Kovács, Á.I. Csincsi, T.Z. Nagy, S. Boros, G. Timári, Z. Novák, Design and application of new imidazolylsulfonate-based benzyne precursor: an efficient triflate alternative, Org. Lett., 14 (2012) 2022-2025.
[7] H. Li, T. Miao, M. Wang, P. Li, L. Wang, Recent advances in exploring diverse decarbonylation, decarboxylation and desulfitation coupling reactions for organic transformations, Synlett., 27 (2016) 1635-1648.
[8a] E. Vessally, A new avenue to the synthesis of highly substituted pyrroles: synthesis from N-propargylamines, RSC Adv., 6 (2016) 18619-18631;
[8b] E. Vessally, H. Saeidian, A. Hosseinian, L. Edjlali, A. Bekhradnia, A review on synthetic applications of oxime esters, Curr.Org. Chem., 21 (2017) 249-271;
[8c] E. Vessally, L. Edjlali, A. Hosseinian, A. Bekhradnia, M.D. Esrafili, Novel routes to quinoline derivatives from N-propargylamines, RSC Adv., 6 (2016) 49730-49746;
[8d] E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M.D. Esrafili, New page to access pyridine derivatives: synthesis from N-propargylamines, RSC Adv., 6 (2016) 71662-71675;
[8e] E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M. D Esrafili, New page to access pyrazines and their ring fused analogues: Synthesis from N-propargylamines, Curr.Org. Synth., 14 (2017) 557-567;
[8f] E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M.D. Esrafili, New route to 1, 4-oxazepane and 1, 4-diazepane derivatives: synthesis from N-propargylamines, RSC Adv., 6 (2016) 99781-99793;
[8g] E. Vessally, S. Soleimani-Amiri, A. Hosseinian, L. Edjlali, A. Bekhradnia, New protocols to access imidazoles and their ring fused analogues: synthesis from N-propargylamines, RSC Adv., 7 (2017) 7079-7091;
[8h] M. Babazadeh, S. Soleimani-Amiri, E. Vessally, A. Hosseinian, L. Edjlali, Transition metal-catalyzed [2+ 2+ 2] cycloaddition of nitrogen-linked 1, 6-diynes: a straightforward route to fused pyrrolidine systems, RSC Adv., 7 (2017) 43716-43736;
[8i] S. Arshadi, E. Vessally, L. Edjlali, R. Hosseinzadeh-Khanmiri, E. Ghorbani-Kalhor, N-Propargylamines: versatile building blocks in the construction of thiazole cores, Beilstein J. Org. Chem., 13 (2017) 625-638;
[8j] E. Vessally, A. Hosseinian, L. Edjlali, E. Ghorbani-Kalhor, R. Hosseinzadeh-Khanmiri, Intramolecular cyclization of N-propargyl anilines: a new synthetic entry into highly substituted indoles, J. Iran. Chem. Soc., 14 (2017) 2339-2353;
[8k] S. Arshadi, E. Vessally, L. Edjlali, E. Ghorbani-Kalhor, R. Hosseinzadeh-Khanmiri, N-Propargylic β-enaminocarbonyls: powerful and versatile building blocks in organic synthesis, RSC Adv., 7 (2017) 13198-13211;
[8l] E. Vessally, A. Hosseinian, L. Edjlali, M. Babazadeh, R. Hosseinzadeh-Khanmiri, New strategy for the synthesis of morpholine cores: synthesis from N-propargylamines, Iran. J. Chem. Chem. Eng., 36 (2017) 1-13;
[8m] S. Arshadi, E. Vessally, M. Sobati, A. Hosseinian, A. Bekhradnia, Chemical fixation of CO2 to N-propargylamines: a straightforward route to 2-oxazolidinones, J. CO2 Util., 19 (2017) 120-129;
[8n] E. Vessally, R. Hosseinzadeh-Khanmiri, E. Ghorbani-Kalhor, M. Es'haghi, A. Bekhradnia, Domino carbometalation/coupling reactions of N-arylpropiolamides: a novel and promising synthetic strategy toward stereocontrolled preparation of highly substituted 3-methyleneindolinones, RSC Adv., 7 (2017) 19061-19072;
[8o] E. Vessally, M. Babazadeh, K. Didehban, A. Hosseinian, L. Edjlali, Intramolecular ipso-Cyclization of N-Arylpropiolamides: A Novel and Straightforward Synthetic Approach for Azaspiro [4.5] decatrien-2-ones, Curr. Org. Chem., 22 (2018) 286-297;
 [9a] S. Soleimani-Amiri, E. Vessally, M. Babazadeh, A. Hosseinian, L. Edjlali, Intramolecular cyclization of N-allyl propiolamides: a facile synthetic route to highly substituted γ-lactams (a review), RSC Adv., 7 (2017) 28407-28418;
[9b] E. Vessally, M. Babazadeh, A. Hosseinian, L. Edjlali, L. Sreerama, Recent Advances in Synthesis of Functionalized β-Lactams through Cyclization of N-Propargyl Amine/Amide Derivatives, Curr. Org. Chem., 22 (2018) 199-205;
[9c] E. Vessally, A. Hosseinian, M. Babazadeh, L. Edjlali, R. Hosseinzadeh-Khanmiri, Metal Catalyzed Carboxylative Coupling of Terminal Alkynes, Organohalides and Carbon Dioxide: A Novel and Promising Synthetic Strategy toward 2-Alkynoates (A Review), Curr. Org. Chem., 22 (2018) 315-322;
[9d] S. Arshadi, E. Vessally, A. Hosseinian, S. Soleimani-amiri, L. Edjlali, Three-component coupling of CO2, propargyl alcohols, and amines: An environmentally benign access to cyclic and acyclic carbamates (A Review), J. CO2 Util., 21 (2017) 108-118;
[9e] E. Vessally, S. Soleimani-Amiri, A. Hosseinian, L. Edjlali, M. Babazadeh, Chemical fixation of CO2 to 2-aminobenzonitriles: a straightforward route to quinazoline-2, 4 (1H, 3H)-diones with green and sustainable chemistry perspectives, J. CO2 Util., 21 (2017) 342-352;
[9f] E. Vessally, M. Babazadeh, A. Hosseinian, S. Arshadi, L. Edjlali, Nanocatalysts for chemical transformation of carbon dioxide, J. CO2 Util., 21 (2017) 491-502;
[9g] E. Vessally, K. Didehban, M. Babazadeh, A. Hosseinian, L. Edjlali, Chemical fixation of CO2 with aniline derivatives: A new avenue to the synthesis of functionalized azole compounds (A review), J. CO2 Util., 21 (2017) 480-490;
[9h] E. Vessally, A. Hosseinian, L. Edjlali, M. Babazadeh, K. Didehban, Chemical Fixation of CO2 to Allylic (α-Allenylic) Amines: A Green Route to Synthesis of Functionalized 2-Oxazolidones, Mini-Rev. Org. Chem., 15 (2018) 315-323;
[9i] A. Hosseinian, M. Babazadeh, L. Edjlali, Z. Rahmani, E. Vessally, Intramolecular Cyclization of Aryl Propargyl Ethers: A Straightforward and Convenient Approach to Benzofuran Derivatives, Curr. Org. Synth., 15 (2018) 972-981;
[9j] K. Didehban, E. Vessally, M. Salary, L. Edjlali, M. Babazadeh, Synthesis of a variety of key medicinal heterocyclic compounds via chemical fixation of CO2 onto o-alkynylaniline derivatives, J. CO2 Util., 23 (2018) 42-50;
[10] A. Hosseinian, S. Farshbaf, L.Z. Fekri, M. Nikpassand, E. Vessally, Cross-Dehydrogenative Coupling Reactions Between P (O)–H and X–H (X= S, N, O, P) Bonds, Top. Curr. Chem., 376 (2018) 23.
[11] F.A.H. Nasab, L.Z. Fekri, A. Monfared, A. Hosseinian, E. Vessally, Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling reactions, RSC Adv., 8 (2018) 18456-18469.
[12] S. Farshbaf, L.Z. Fekri, M. Nikpassand, R. Mohammadi, E. Vessally, Dehydrative condensation of β-aminoalcohols with CO 2: An environmentally benign access to 2-oxazolidinone derivatives, J. CO2 Util., 25 (2018) 194-204.
[13] A. Hosseinian, S. Ahmadi, A. Monfared, P.D. Nezhad, E. Vessally, Nano-structured Catalytic Systems in Cyanation of Aryl Halides with K4 [Fe (CN) 4], Curr. Org. Chem., 22 (2018) 1862-1874.
[14] A. Hosseinian, L. Zare Fekri, A. Monfared, E. Vessally, M. Nikpassand, Transition-metal-catalyzed C–N cross-coupling reactions of N-unsubstituted sulfoximines: a review, J. Sulfur Chem., 39 (2018) 674-698.
[15] K. Nejati, S. Ahmadi, M. Nikpassand, P.D.K. Nezhad, E. Vessally, Diaryl ethers synthesis: nano-catalysts in carbon-oxygen cross-coupling reactions, RSC Adv., 8 (2018) 19125-19143.
[16] A. Hosseinian, S. Ahmadi, F.A.H. Nasab, R. Mohammadi, E. Vessally, Cross-Dehydrogenative C–H/S–H Coupling Reactions, Top. Curr. Chem., 376 (2018) 39.
[17] E. Vessally and M. Abdoli, Oxime ethers as useful synthons in the synthesis of a number of key medicinal heteroaromatic compounds,J. Iran. Chem. Soc., 13 (2016) 1235–1256.
[18] A. Hosseinian, S. Farshbaf, R. Mohammadi, A. Monfared, E. Vessally, Advancements in six-membered cyclic carbonate (1, 3-dioxan-2-one) synthesis utilizing carbon dioxide as a C1 source, RSC Adv., 8 (2018) 17976-17988.
[19] N. Rodriguez, L.J. Goossen, Decarboxylative coupling reactions: a modern strategy for C–C-bond formation, Chem. Soc. Rev. 40 (2011) 5030-5048.
[20] A. Hosseinian, F.A.H. Nasab, S. Ahmadi, Z. Rahmani, E. Vessally, Decarboxylative cross-coupling reactions for P (O)–C bond formation, RSC Adv. 8 (2018) 26383-26398.
[21] A. Hosseinian, P.D.K. Nezhad, S. Ahmadi, Z. Rahmani, A. Monfared, A walk around the decarboxylative CS cross-coupling reactions, J. Sulfur Chem. 39 (2018) DOI: 10.1080/17415993.2018.1515314.
[22] L.J. Goossen, K. Gooßen, Decarboxylative coupling reactions, Top. Organomet. Chem. 44 (2013) 121–142.
[23] D. Katayev, B. Exner, L.J. Goossen, Synthesis of biaryls by decarboxylative Hiyama coupling, ChemCatChem, 7 (2015) 2028-2032.
[24] G.C. Edwin Raja, F.M. Irudayanathan, H.S. Kim, J. Kim, S. Lee, Nickel-catalyzed Hiyama-type decarboxylative coupling of propiolic acids and organosilanes, J. Org. Chem. 81 (2016) 5244-5249.
[25] J. Jang, G.C.E. Raja, J.H. Lee, Y. Son, J. Kim, S. Lee, Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes, Tetrahedron Lett, 57 (2016) 4581-4584.
[26] K. Cheng, C. Wang, Y. Ding, Q. Song, C. Qi, X.M. Zhang, Hiyama cross-coupling of arenediazonium salts under mild reaction conditions, J. Org. Chem. 76 (2011) 9261-9268.
[27] K. Cheng, B. Zhao, S. Hu, X.M. Zhang, C. Qi, Pd-catalyzed cross-coupling reactions of arenediazonium salts with arylsilanes and aryltrifluoroborates in water, Tetrahedron Lett. 54 (2013) 6211-6214.
[28] H. Zhang, C. Wang, Z. Li, Z. Wang, Palladium-catalyzed denitrogenative Hiyama cross-coupling with arylhydrazines under air, Tetrahedron Lett. 56 (2015) 5371-5376.
[29] Y. Li, W. Liu, Q. Tian, Q. Yang, C. Kuang, Palladium‐catalyzed Suzuki cross‐coupling of phenylhydrazine or (phenylsulfonyl) hydrazine, Eur. J. Org. Chem. 2014 (2014) 3307-3312.
[30] K. Yuan, J.F.O. Soulé, H. Doucet, Functionalization of C–H bonds via metal-catalyzed desulfitative coupling: an alternative tool for access to aryl-or alkyl-aubstituted (hetero) arenes, ACS Catal, 5 (2015) 978-991.
 
[31] K. Cheng, S. Hu, B. Zhao, X.M., Zhang, C. Qi, Palladium-catalyzed Hiyama-type cross-coupling reactions of arenesulfinates with organosilanes, J. Org. Chem., 78 (2013) 5022-5025.
[32] W. Zhang, F. Liu, K. Li, B. Zhao, Pd‐catalyzed desulfitative Hiyama coupling with sulfonyl chlorides, Appl. Organomet. Chem. 28 (2014) 379-381.
[33] H. Miao, F. Wang, S. Zhou, G. Zhang, Y. Li, Palladium-catalyzed Hiyama coupling reaction of arylsulfonyl hydrazides under oxygen, Org. Biomol. Chem. 13 (2015) 4647-4651.