Department of Chemistry
Indian Institute of Technology Delhi

Transition-Metal-Catalyzed C–H Bond Polyfunctionalization of (Hetero)Arenes

Dr. Jean-François Soulé
Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France

Date: January 19th 2018 (Friday)
Time: 4 PM
Venue: Committee Room, Chemistry Department, 6th Floor

Transition-metal-mediated direct coupling via C-H bond cleavage is currently one of the most active areas in organic synthesis. We found that appropriately heteroaromatic substrates such as thiophenes, selenophenes, pyrroles, and benzoxazoles can undergo palladium catalyzed direct coupling with benzenesulfonyl chlorides and/or aryl bromides via regioselective C-H bond cleavage.1 In this context, we have developed methods that can target multiple different sites on heterocycles using catalyst and/ or reagent control to define simultaneously how each site is modified.1,2 Such procedure was applied in the synthesis of polycyclic organic molecules as well as polycyclic aromatic hydrocarbons.3 As an example, we recently reported the syntheses of phenanthro[9,10-b]thiophene derivatives from simple thiophenes, 2-bromobenzene sulfonyl chlorides and aryl bromides via three C–H bond arylations reactions.6 Similar strategy was applied for the synthesis of dibenzo[j,l]fluoranthene. Recently, we applied performed the late stage modification of ligands such as fulvenes,4 arylphosphine oxides5 or pyridine derivatives6 by C–H bond functionalizations The details of these new reactions will be described in this lecture.

  1. a) R. Jin, K. Yuan, E. Chatelain, J.-F. Soulé, H. Doucet, Adv. Synth. Catal. 2014, 356, 3831; b) A. Skhiri, R. B. Salem, J.-F. Soulé, H. Doucet, Chem. Eur. J. 2017, 23, 2788; c) K. Yuan, J.-F. Soulé, H. Doucet, ACS Catal. 2015, 5, 978; d) F. Abdellaoui, C. Youssef, H. Ben Ammar, T. Roisnel, J.-F. Soulé, H. Doucet, ACS Catal. 2016, 6, 4248.
  2. K. Yuan, J.-F. Soulé, V. Dorcet, H. Doucet, ACS Catal. 2016, 8121.
  3. a) W. Hagui, N. Besbes, E. Srasra, T. Roisnel, J.-F. Soulé, H. Doucet, Org. Lett. 2016, 18, 4182; b) X. Shi, J.-F. Soulé, H. Doucet, J. Org. Chem. 2017, 82, 3886; c) X. Shi, T. Roisnel, J.-F. Soulé, H. Doucet, Org. Chem. Front. 2018, advance article.
  4. M. Brahim, H. Ben Ammar, V. Dorcet, J.-F. Soulé, H. Doucet, Org. Lett. 2017, 19, 2584.
  5. C.-S. Wang, P. H. Dixneuf, J.-F. Soulé, ChemCatChem 2017, 9, 31176. a) C.-S. Wang, X.-F. Wu, P. H. Dixneuf, J.-F. Soulé, ChemSusChem 2017, 10, 3075; b) C.-S. Wang, T. Roisnel, P. H. Dixneuf, J.-F. Soulé, Org. Lett. 2017, advance article

All are cordially invited to attend.
Convener (Seminars)