Metal-Free Arylation of Phenols and Carboxylic Acids

Metal-Free Arylation of Phenols and Carboxylic Acids

Olofsson, Berit

Abstract:

Diaryl ethers and aryl esters are common structural features in pharmaceuticals, agrochemicals, polymers and numerous natural products. Despite more than a century of immense focus on finding efficient synthetic routes to these compound classes, the synthesis of substituted diaryl ethers and aryl esters remain difficult. The use of diaryliodonium salts has recently gained considerable attention in organic synthesis. Their properties allow for both metal-catalyzed and metalfree reactions, avoiding the drawbacks of organometallic chemistry, such as cost, toxicity, and threshold values in pharmaceutical products. We have developed several efficient one-pot routes to diaryliodonium salts, and these compounds are now inexpensive and easily available (Scheme 1). We are presently investigating these selective and nontoxic reagents as electrophilic arylating agents, and herein we present our results on the arylation of phenols and carboxylic acids.

Diaryl ethers and aryl esters are common structural features in pharmaceuticals, agrochemicals, polymers and numerous natural products. Despite more than a century of immense focus on finding efficient synthetic routes to these compound classes, the synthesis of substituted diaryl ethers and aryl esters remain difficult. The use of diaryliodonium salts has recently gained considerable attention in organic synthesis. Their properties allow for both metal-catalyzed and metalfree reactions, avoiding the drawbacks of organometallic chemistry, such as cost, toxicity, and threshold values in pharmaceutical products. We have developed several efficient one-pot routes to diaryliodonium salts, and these compounds are now inexpensive and easily available (Scheme 1). We are presently investigating these selective and nontoxic reagents as electrophilic arylating agents, and herein we present our results on the arylation of phenols and carboxylic acids.

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DOI: 10.5151/chempro-14bmos-R0184-1

Referências bibliográficas

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• [3] 3 a) Bielawski, M.; Aili, D.; Olofsson, B. J. Org. Chem. 2008, 73, 4602. b) Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610. c) Merritt, E. A.; Malmgren, J.; Klinke, F. J.; Olofsson, B. Synlett 2009, 2277. d) Zhu, M.; Jalalian, N.; Olofsson, B. Synlett 2008, 592.
• [4] 4 a) Norrby, P.-O.; Petersen, T. B.; Bielawski, M.; Olofsson, B. Chem. Eur. J. 2010, 16, 8251. b) Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett. 2011, 13, 1552. c) Petersen, T. B.; Khan, R.; Olofsson, B. Submitted.

Como citar:

Olofsson, Berit; "Metal-Free Arylation of Phenols and Carboxylic Acids", p-184-184. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0184-1