Stig D. Friis

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Rapid and Efficient Conversion of ¹¹CO₂ to ¹¹CO through Silacarboxylic Acids: Applications in Pd‐Mediated Carbonylations

Chemistry - A European Journal (2015)

Patrik Nordeman Stig D. Friis T. Andersen Hélène Audrain Mats Larhed

Herein, we present a new rapid, efficient, and low-cost radiosynthetic protocol for the conversion of (11) CO2 to (11) CO and its subsequent application in Pd-mediated reactions of importance for PET applications. This room-temperature methodology, using readily available chemical reagents, is carried out in simple glass vials, thus eliminating the need for expensive and specialized high-temperature equipment to access (11) CO. With this fast and near-quantitative conversion of (11) CO2 into (11) CO, aryl and heteroaryl iodides were easily converted into a broad selection of biologically active amides in radiochemical yields ranging from 29-84 %.

10.1002/chem.201503262

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Citations (32)

CCDC 1406399: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Xin Zhuo Camille Lescot Stig D. Friis Kim Daasbjerg 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/cc1j6gqx

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Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

Angewandte Chemie (2015)

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

Abstract The first organocatalyzed trapping of CO 2 through CC and CO bond formation is reported. Alkynyl indoles together with catalytic amounts of an organic base and five equivalents of CO 2 resulted in the formation new heterocyclic structures. These tricyclic indole‐containing products were successfully prepared under mild reaction conditions from aromatic, heteroaromatic, and aliphatic alkynyl indoles with complete regioselectivity. Further investigations suggest that CC bond formation is the initial intermolecular step, followed by lactone‐forming CO bond formation.

10.1002/ange.201500233

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Citations (22)

Cobalt-catalysed C–H methylation for late-stage drug diversification

Nature Chemistry (2020)

Stig D. Friis Magnus J. Johansson Lutz Ackermann

Functional group

Reactivity

10.1038/s41557-020-0475-7

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Citations (188)

ChemInform Abstract: Metal‐Free Halonium Mediated Acetate Shifts of Ynamides to Access α‐Halo Acrylamides/Acrylimides.

ChemInform (2011)

Soeren Kramer Stig D. Friis Xin Zhuo Yann Odabachian Troels Skrydstrup

Abstract The reaction allows access to α‐iodo, bromo and chloro acrylamides/acrylimides using the same conditions and halosuccinimides.

10.1002/chin.201127079

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A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl–Aryl Cross‐Coupling of Aryl Halides and Olefins

Angewandte Chemie International Edition (2017)

Stig D. Friis Michael T. Pirnot Lauren N. Dupuis Stephen L. Buchwald

Abstract We report an efficient means of sp 2 –sp 3 cross coupling for a variety of terminal monosubstituted olefins with aryl electrophiles using Pd and CuH catalysis. In addition to its applicability to a range of aryl bromide substrates, this process was also suitable for electron‐deficient aryl chlorides, furnishing higher yields than the corresponding aryl bromides in these cases. The optimized protocol does not require the use of a glovebox and employs air‐stable Cu and Pd complexes as precatalysts. A reaction on 10 mmol scale further highlighted the practical utility of this protocol. Employing a similar protocol, a series of cyclic alkenes were also examined. Cyclopentene was shown to undergo efficient coupling under these conditions. Lastly, deuterium‐labeling studies indicate that deuterium scrambling does not take place in this sp 2 ‐sp 3 cross coupling, implying that β‐hydride elimination is not a significant process in this transformation.

10.1002/anie.201703400

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Citations (106)

Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis

Journal of the American Chemical Society (2016)

Stig D. Friis Michael T. Pirnot Stephen L. Buchwald

Detailed in this Communication is the enantioselective synthesis of 1,1-diarylalkanes, a structure found in a range of pharmaceutical drug agents and natural products, through the employment of copper(I) hydride and palladium catalysis. Judicious choice of ligand for both Cu and Pd enabled this hydroarylation protocol to work for an extensive array of aryl bromides and styrenes, including β-substituted vinylarenes and six-membered heterocycles, under relatively mild conditions.

10.1021/jacs.6b04566

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Citations (234)

Palladium-catalysed carbonylative α-arylation of nitromethane

Chemical Communications (2015)

Zhong Lian Stig D. Friis Troels Skrydstrup

A palladium-catalysed approach to α-nitroketonesviacarbonylative α-arylation of nitromethane is presented, thus providing easy access to key intermediates and important heterocycles.

Carbonylation

10.1039/c5cc00123d

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Citations (29)

Palladium‐Catalyzed Carbonylative α‐Arylation of 2‐Oxindoles with (Hetero)aryl Bromides: Efficient and Complementary Approach to 3‐Acyl‐2‐oxindoles

Angewandte Chemie (2014)

Zhong Lian Stig D. Friis Troels Skrydstrup

Abstract An efficient Pd‐catalyzed carbonylative α‐arylation of 2‐oxindoles with aryl and heteroaryl bromides for the one‐step synthesis of 3‐acyl‐2‐oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the more common oxindole forming reactions. The transformation only requires a mild base and provides good to excellent yields even with heteroaromatic substrates. Employing a near stoichiometric amount of 13 COgen, the methodology was easily extended to [ 13 C] acyl labeling. The general applicability of the reaction conditions was demonstrated in the synthesis of a structure related to the pharmaceutically active 3‐acyl‐2‐oxindoles, tenidap.

Oxindole

Stoichiometry

Reaction conditions

Base (topology)

Carbonylation

10.1002/ange.201404217

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Citations (8)

CCDC 1056293: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Thomas Levin Andersen Stig D. Friis Hélène Audrain Patrik Nordeman Gunnar Antoni

Crystal (programming language)

10.5517/cc14g4zq

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Citations (0)