NDLI: Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00675f Click here for additional data file.

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Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00675f Click here for additional data file.

Content Provider	Semantic Scholar
Author	Markovic, Tim Z. Rocke, Benjamin N. Blakemore, David C. Mascitti, Vincent Willis, Michael C.
Copyright Year	2017
Abstract	Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon-carbon bonds in the pharmaceutical industry, the Suzuki-Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfinates, a cross-coupling process of unrivalled scope and utility is realized. The corresponding 3- and 4-substituted pyridine variants are also efficient coupling partners. In addition, we apply these sulfinates in a library format to the preparation of medicinally relevant derivatives of the drugs varenicline (Chantix) and mepyramine (Anthisan).
Starting Page	4437
Ending Page	4442
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/c7sc00675f
PubMed reference number	28936330
Journal	Medline
Volume Number	8
Alternate Webpage(s)	http://www.rsc.org/suppdata/c7/sc/c7sc00675f/c7sc00675f1.pdf
Alternate Webpage(s)	http://pubs.rsc.org/en/content/articlepdf/2017/SC/C7SC00675F
Alternate Webpage(s)	https://doi.org/10.1039/c7sc00675f
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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Supporting Information Pyridine Sulfinates as General Nucleophilic Coupling Partners in Palladium- Catalyzed Cross-Coupling Reactions with Aryl Halides

Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03106g Click here for additional data file.

Palladium-catalyzed difluoromethylation of heteroaryl chlorides, bromides and iodides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00691h Click here for additional data file.

Dynamic multicolor protein labeling in living cells† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01364g Click here for additional data file. Click here for additional data file. Click here for additional data file.

C–H functionalization of amines with aryl halides by nickel-photoredox catalysis† †Electronic supplementary information (ESI) available: Experimental details and characterization data. See DOI: 10.1039/c6sc02815b Click here for additional data file.

Kinase-templated abiotic reaction† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01416c Click here for additional data file.

Enantioselective propargylic [1,3]-rearrangements: copper-catalyzed O-to-N migrations toward C–N bond formation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01042g Click here for additional data file. Click here for additional data file.

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03337j Click here for additional data file.

Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04585e Click here for additional data file.

Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00675f Click here for additional data file.

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Supporting Information Pyridine Sulfinates as General Nucleophilic Coupling Partners in Palladium- Catalyzed Cross-Coupling Reactions with Aryl Halides

Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03106g Click here for additional data file.

Palladium-catalyzed difluoromethylation of heteroaryl chlorides, bromides and iodides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00691h Click here for additional data file.

Dynamic multicolor protein labeling in living cells† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01364g Click here for additional data file. Click here for additional data file. Click here for additional data file.

C–H functionalization of amines with aryl halides by nickel-photoredox catalysis† †Electronic supplementary information (ESI) available: Experimental details and characterization data. See DOI: 10.1039/c6sc02815b Click here for additional data file.

Kinase-templated abiotic reaction† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01416c Click here for additional data file.

Enantioselective propargylic [1,3]-rearrangements: copper-catalyzed O-to-N migrations toward C–N bond formation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01042g Click here for additional data file. Click here for additional data file.

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03337j Click here for additional data file.

Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04585e Click here for additional data file.

Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00675f Click here for additional data file.