Microwave-Assisted Synthesis of Heterocycles via Rhodium(III)-Catalyzed C–H Activation: Norbornadiene as an Acetylene EquivalentClick to copy article linkArticle link copied!
- Joyann S. DonaldsonJoyann S. DonaldsonPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Joyann S. Donaldson
- Haojun JiangHaojun JiangBioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. ChinaMore by Haojun Jiang
- Dehuan KongDehuan KongBioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. ChinaMore by Dehuan Kong
- Wei LiWei LiBioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. ChinaMore by Wei Li
- Indrawan J. McAlpineIndrawan J. McAlpinePfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Indrawan J. McAlpine
- Sajiv K. NairSajiv K. NairPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Sajiv K. Nair
- Sylvie SakataSylvie SakataPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Sylvie Sakata
- Jillian E. SpanglerJillian E. SpanglerPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Jillian E. Spangler
- Nicole SunNicole SunBioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. ChinaMore by Nicole Sun
- Michelle B. Tran-DubéMichelle B. Tran-DubéPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Michelle B. Tran-Dubé
- Yang ZhouYang ZhouBioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. ChinaMore by Yang Zhou
- Ryan L. Patman*Ryan L. Patman*E-mail: [email protected]Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United StatesMore by Ryan L. Patman
Abstract

General procedures for the rhodium-catalyzed annulation of aryl/heteroaryl O-pivaloyl hydroxamic acids and norbornadiene have been developed. Employing norbornadiene as an acetylene equivalent enables utilization of diverse heterocyclic substrates for this transformation which fail to react or undergo competitive Lossen rearrangement under previously reported conditions. Microwave heating significantly reduces reaction times compared to conventional protocols and allows a one-step process to be realized. The conditions described herein have been adapted for gram-scale synthesis and applied to the formal synthesis of Pfizer clinical candidates.
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