I am a professor of Organic Chemistry, and serve as the Dean of Chemistry since 2019. I am also the chair of the steering board of SUCCeSS; Stockholm University Center for Circular and Sustainable Systems.
- Member of the Angew. Chem. International advisory board since 2020.
- Elected as a Chemistry Europe Fellow in 2018.
- Secretary and vice chair of the Division of Organic Chemistry in EuCheMS since 2018.
- Vice chair of the International Scientific Committee of the European Symposium on Organic Chemistry (ESOC) since 2017
- Board Member of Carl Trygger Foundation (CTS) since 2017
- Spent 3 months in Stellenbosch, South Africa as a STIAS Fellow (2014 - 2015).
- Member of the International Scientific Committee of the Hypervalent Iodine conference series (ICHIC) since 2010.
I have a PhD from KTH (Stockholm) on asymmetric, divergent synthesis of vicinal amino alcohols via vinylepoxides and vinylaziridines (with Peter Somfai, 1998-2002).
Post doc studies at Bristol University, UK with Varinder K. Aggarwal in 2003-2004. The project started out as a total synthesis of (-)-Epibatidine including methodology development of alfa-arylation of ketones. Returning to Sweden, I became assistant supervisor in the group of Prof. J.-E. Bäckvall at Stockholm University (SU).
I started my independent career in 2006, with a position as Assistant Professor at SU. I became "Docent" in March 2008, and got a permanent position as Associate Professor (Lektor) in 2009. I was promoted to Full Professor in 2013.
- Development of Efficient Synthetic Methodology for Hypervalent Iodine Reagents
- Development of Metal-Free Application Areas for Hypervalent Iodine Reagents
- Application of Developed Methodology in Total Synthesis of Natural Products
Some of our most cited publications:
Eleanor A. Merritt and Berit Olofsson*
Diaryliodonium salts – from Obscurity to Fame
Angew. Chem. Int. Ed. 2009, 48, 9052-9070. Link (>860 citations)
Marcin Bielawski, Mingzhao Zhu and Berit Olofsson*
Efficient and General One-Pot Synthesis of Diaryliodonium Triflates: Scope and Limitations
Adv. Synth. Catal. 2007, 349, 2610-2618. Link (>330 citations)
Frithjof C. Küpper,* Martin C. Feiters, Berit Olofsson, Tatsuo Kaiho, Shozo Yanagida, Michael B. Zimmermann, Lucy J. Carpenter, George W. Luther III, Zunli Lu, Mats Jonsson and Lars Kloo
Commemorating two centuries of iodine research: An interdisciplinary overview of current research
Angew. Chem. Int. Ed. 2011, 50, 11598-11620. Link (>270 citations)
Marcin Bielawski, David Aili and Berit Olofsson*
Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides
J. Org. Chem. 2008, 73, 4602-4607. Link (>240 citations)
Joel Malmgren, Stefano Santoro, Nazli Jalalian, Fahmi Himo* and Berit Olofsson* Arylation with Unsymmetrical Diaryliodonium Salts – a Chemoselectivity Study
Chem. Eur. J. 2013, 19, 10334-10342. Link (>200 citations)
Nazli Jalalian, Eloisa E. Ishikawa, Luiz F. Silva Jr. and Berit Olofsson*
Room Temperature, Metal-Free Synthesis of Diaryl Ethers with Use of Diaryliodonium Salts
Org. Lett. 2011, 13, 1552-1555. Link (>170 citations)
A selection from Stockholm University publication database
Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions
2020. Laura Castoldi (et al.). Angewandte Chemie International Edition 59 (36), 15512-15516Article
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions
2018. Nibadita Purkait (et al.). Angewandte Chemie International Edition 57 (35), 11427-11431Article
A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.
Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides
2018. Piret Villo, Gabriella Kervefors, Berit Olofsson. Chemical Communications 54 (64), 8810-8813Article
Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.
Competing Pathways in O-Arylations with Diaryliodonium Salts
2017. Elin Stridfeldt (et al.). Chemistry - A European Journal 23 (53), 13249-13258Article
A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.
Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents
2016. Gergely L. Tolnai, Ulf J. Nilsson, Berit Olofsson. Angewandte Chemie International Edition 55 (37), 11226-11230Article
Novel methodology for O-functionalization of carbohydrate derivatives has been established using bench-stable and easily prepared iodonium(III) reagents. Both electron-withdrawing and electron-donating aryl groups were introduced under ambient conditions and without precautions to exclude air or moisture. Furthermore, the approach was extended both to full arylation of cyclodextrin, and to trifluoroethylation of carbohydrate derivatives. This is the first general approach to introduce traditionally non-electrophilic groups into any of the OH groups around the sugar backbone. The methodology will be useful both in synthetic organic chemistry and biochemistry, as important functional groups can be incorporated under simple and robust reaction conditions in a fast and efficient manner.
One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts
2016. Marcus Reitti, Piret Villo, Berit Olofsson. Angewandte Chemie International Edition 55 (31), 8928-8932Article
A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryl-iodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.
Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents
2016. Elin Stridfeldt (et al.). Chemistry - A European Journal 22 (45), 16066-16070Article
A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl) iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.
Diaryliodonium salts: A journey from obscurity to fame
2009. Eleanor A. Merritt, Berit Olofsson. Angewandte Chemie International Edition 48 (48), 9052-9070Article
The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent of novel, facile, and efficient synthetic routes to these compounds, many more applications can be foreseen. Herein we provide an overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts.
Arylation with Diaryliodonium Salts
2016. Berit Olofsson. Hypervalent Iodine Chemistry, 135-166Chapter
This chapter focuses on recent developments in metal-free and metal-catalyzed arylations with diaryliodonium salts (diaryl-λ3-iodanes). Synthetic routes to diaryliodonium salts are briefly described, and chemoselectivity trends with unsymmetric iodonium salts are discussed.
Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts
2011. Nazli Jalalian (et al.). Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011Conference
Diaryl ethers are common structural features in numerous natural products and biol. active compds. Despite more than a century of immense focus on finding efficient synthetic routes to this compd. class, diaryl ethers remain difficult to obtain. Routes that are catalytic in copper have been developed, but high catalyst loadings, excess reagents, elevated temps. and long reaction times are still needed. Pd-catalyzed cross-couplings of phenols and aryl halides at temps. up to 100 °C have recently been reported to give high yields of diaryl ethers. Diaryliodonium salts are non-toxic alternatives to transition metals in the synthesis of diaryl ethers and we have recently developed effective synthetic routes to these salts. Herein we report a fast, high-yielding synthesis of diaryl ethers. The reaction conditions are mild, metal-free, and avoid the use of halogenated solvents, additives, or excess reagents. Precautions to avoid air or moisture are not needed. The scope includes ortho- and halo-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols .
Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides
2008. Marcin Bielawski, David Aili, Berit Olofsson. Journal of Organic Chemistry 73 (12), 4602-4607Article
Diaryliodonium salts have recently received considerable attention as mild arylation reagents in organic synthesis. This paper describes a regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations. The protocol is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.
Efficient and general one-pot synthesis of diaryliodonium triflates: scope and limitations
2007. Marcin Bielawski, Mingzhao Zhu, Berit Olofsson. SIS Report, 19-22Conference
Show all publications by Berit Olofsson at Stockholm University