Palladium catalyzed C–C and C–N bond forming reactions: an update on the synthesis of pharmaceuticals from 2015–2020

Author(s): Jayachandra Rayadurgam ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Sravani Sana ⁶ ^, ⁷ ^, ⁸ ^, ⁹ , M. Sasikumar ¹⁰ ^, ¹¹ ^, ¹² ^, ⁹ , Qiong Gu ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2021

Journal: Organic Chemistry Frontiers

Publisher: Royal Society of Chemistry (RSC)

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Abstract

Some of the most prominent and promising catalysts in organic synthesis for the requisite construction of C–C and C–N bonds are palladium (Pd) catalysts, which play a pivotal role in pharmaceutical and medicinal chemistry. Their wide range of selectivities, mild reaction conditions, and simple, efficient, and economical protocols make them desirable for the synthesis of highly functionalized molecules, medicinally important intermediates, pharmaceuticals, and agro-products. Researchers from academia and the pharmaceutical industry have also utilized a wide variety of Pd-catalysts for the synthesis of pharmaceuticals on a small and large scale. This review describes pharmaceuticals approved by the United States Food and Drug Administration (the U.S. FDA) between 2015 and 2020, which were synthesized via Pd-catalyzed cross-coupling reactions for the construction of carbon–carbon (C–C) and carbon–nitrogen (C–N) bonds. The review includes both medicinal chemistry routes and patented routes on a bulk scale. Along with details of the synthetic protocols of coupling reactions, the medicinal properties of each approved drug are discussed.

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Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Xiao Chen, Keary M Engle, Dong-Hui Wang … (2009)

In the past decade, palladium-catalyzed C-H activation/C-C bond-forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross-coupling reactions using aryl and alkyl halides. This Review begins with a brief introduction of four extensively investigated modes of catalysis for forming C-C bonds from C-H bonds: Pd(II)/Pd(0), Pd(II)/Pd(IV), Pd(0)/Pd(II)/Pd(IV), and Pd(0)/Pd(II) catalysis. A more detailed discussion is then directed towards the recent development of palladium(II)-catalyzed coupling of C-H bonds with organometallic reagents through a Pd(II)/Pd(0) catalytic cycle. Despite the progress made to date, improving the versatility and practicality of this new reaction remains a tremendous challenge.

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Alpelisib for PIK3CA-Mutated, Hormone Receptor–Positive Advanced Breast Cancer

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PIK3CA mutations occur in approximately 40% of patients with hormone receptor (HR)-positive, human epidermal growth factor receptor 2 (HER2)-negative breast cancer. The PI3Kα-specific inhibitor alpelisib has shown antitumor activity in early studies.