Stig D. Friis

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc14g50s

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HTE as a Tool in C–H Activation Reaction Discovery and Late-Stage Functionalization of Pharmaceuticals

ACS symposium series (2022)

Stig D. Friis Erik Weis Magnus J. Johansson

Herein we will discuss how HTE can facilitate not only the development of new reaction manifolds, but also how to design HTE experiments to gain further understanding useful in medicinal chemistry efforts and late-stage functionalization. Case studies on cobalt-catalyzed C–H methylation and iridium-catalyzed C–H amination using drugs as substrates are presented. Moving towards more sustainable ways of working in drug discovery we also showcase how new dispensing techniques can considerably add to miniaturization of reaction development.

Surface Modification

10.1021/bk-2022-1420.ch010

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ChemInform Abstract: Palladium‐Catalyzed Carbonylation of Aryl Bromides with N‐Substituted Cyanamides

ChemInform (2014)

Zhong Lian Stig D. Friis Anders T. Lindhardt Troels Skrydstrup

Abstract The carbonylation is performed using a slight excess of CO‐gas which is produced ex situ from (II) in a two‐chamber reaction system.

Carbonylation

10.1002/chin.201449076

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CCDC 842746: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Stephanie N. Kramer Stig D. Friis Xin Zhuo Yann Odabachian Troels Skrydstrup

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccx8ycg

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Late-stage synthesis of heterobifunctional molecules for PROTAC applications via ruthenium-catalysed C‒H amidation

Nature Communications (2023)

Daniele Antermite Stig D. Friis Johan R. Johansson Okky Dwichandra Putra Lutz Ackermann

Abstract PROteolysis TArgeting Chimeras (PROTACs) are heterobifunctional molecules emerging as a powerful modality in drug discovery, with the potential to address outstanding medical challenges. However, the synthetic feasibility of PROTACs, and the empiric and complex nature of their structure-activity relationships continue to present formidable limitations. As such, modular and reliable approaches to streamline the synthesis of these derivatives are highly desirable. Here, we describe a robust ruthenium-catalysed late-stage C‒H amidation strategy, to access fully elaborated heterobifunctional compounds. Using readily available dioxazolone reagents, a broad range of inherently present functional groups can guide the C–H amidation on complex bioactive molecules. High selectivity and functional group tolerance enable the late-stage installation of linkers bearing orthogonal functional handles for downstream elaboration. Finally, the single-step synthesis of both CRBN and biotin conjugates is demonstrated, showcasing the potential of this methodology to provide efficient and sustainable access to advanced therapeutics and chemical biology tools.

Chemical Biology

10.1038/s41467-023-43789-9

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Citations (6)

ChemInform Abstract: Pd‐Catalyzed Carbonylative Access to Aroyl Phosphonates from (Hetero)aryl Bromides.

ChemInform (2015)

Zhong Lian Hongfei Yin Stig D. Friis Troels Skrydstrup

Abstract This is the first transition‐metal catalyzed carbonylation with a phosphorus nucleophile.

Carbonylation

10.1002/chin.201539172

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CCDC 2251355: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Daniele Antermite Stig D. Friis Johan R. Johansson Okky Dwichandra Putra Lutz Ackermann

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2fkqc3

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ChemInform Abstract: Organocatalyzed CO₂ Trapping Using Alkynyl Indoles.

ChemInform (2015)

Xin Zhuo Camille Lescot Stig D. Friis Kim Daasbjerg Troels Skrydstrup

Abstract This first organocatalyzed trapping of CO 2 gives access to new heterocyclic structures.

10.1002/chin.201539115

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CCDC 842747: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Stephanie N. Kramer Stig D. Friis Xin Zhuo Yann Odabachian Troels Skrydstrup

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccx8ydh

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Ruthenium-catalysed C‒H amidation for the late-stage synthesis of PROTACs

Daniele Antermite Stig D. Friis Johan R. Johansson Okky Dwichandra Putra Lutz Ackermann

PROteolysis TArgeting Chimeras (PROTACs) are a powerful modality in drug discovery, offering the potential to address outstanding medical challenges. However, the synthetic feasibility of PROTACs, and the empiric and complex nature of their structure-activity relationships continue to present formidable limitations. As such, modular and reliable approaches to streamline the synthesis of these compounds are highly desirable. Here, we describe a robust ruthenium-catalysed late-stage C‒H amidation strategy, to provide modular access to both fully elaborated PROTACs and drug conjugates. Using readily available dioxazolone reagents, a broad range of inherently present functional groups can guide the C–H amidation on complex bioactive molecules. High selectivity and functional group tolerance enable the late-stage installation of linkers bearing orthogonal functional handles for downstream elaboration. Finally, the single-step synthesis of PROTAC and biotin conjugates is demonstrated, showcasing the potential of this methodology to provide efficient and sustainable access to advanced therapeutics and chemical biology tools.

10.26434/chemrxiv-2023-669wc

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