Miyaura borylation/Suzuki–Miyaura coupling (MBSC) sequence of 4-bromo-2,4′-bithiazoles with halides: straightforward access to a heterocylic cluster of d-series of thiopeptide GE2270

Literature Information

Publication Date 2018-01-02
DOI 10.1039/C7OB02866K
Impact Factor 3.876
Authors

Pierrik Lassalas, Christophe Berini, Jean-Baptiste E. Y. Rouchet, Jonathan Hédouin, Francis Marsais, Cédric Schneider, Christine Baudequin, Christophe Hoarau


View Original

Abstract

Herein, palladium-catalyzed Miyaura borylation of 4-bromo-2,4′-bithiazoles followed by Suzuki–Miyaura cross-coupling reaction (named the MBSC process) with (hetero)aryl- and alkenyl halides is reported. This methodology offers rapid access to various 2′,4-disubstituted 2,4′-bithiazole features including naturally-occurring 4-alkenylated and 4-pyridinylated 2,4′-bithiazoles. To prove its application, a concise approach for the synthesis of a heterocyclic cluster of the thiopeptide D-series antibiotic GE2270 is reported through a late-stage MBSC strategy.

Related Literature

Surface state engineering of molecule–molecule interactions

Geoffrey Rojas, Scott Simpson, Xumin Chen, Donna A. Kunkel, Justin Nitz, Jie Xiao, Peter A. Dowben, Eva Zurek, Axel Enders

2012-02-20 Paper

DOI: 10.1039/C2CP40254H

Macromolecular architectures for organic photovoltaics

Bhooshan C. Popere, Andrea M. Della Pelle, Ambata Poe, S. Thayumanavan

2012-01-11 Perspective

DOI: 10.1039/C2CP23422J

Al2O3(110) surface as a template for the ordered growth of Ni and Co nanoclusters

Krithika Venkataramani, Thomas N. Jensen, Stig Helveg, Michael Reichling, Flemming Besenbacher, Jeppe V. Lauritsen

2012-01-09 Paper

DOI: 10.1039/C2CP22712F

Covalent bond orders and atomic anisotropies from iterated stockholder atoms

Richard J. Wheatley, Angelica A. Gopal

2011-12-14 Paper

DOI: 10.1039/C2CP23504H

Sea urchin TiO2–nanoparticle hybrid composite photoelectrodes for CdS/CdSe/ZnS quantum-dot-sensitized solar cells

Eui-Hyun Kong, Yong-June Chang, Yoon-Cheol Park, Yeon-Hee Yoon, Hyun-Jin Park, Hyun Myung Jang

2012-02-08 Paper

DOI: 10.1039/C2CP24106D

Back cover

Front/Back Matter

DOI: 10.1039/C2CP90039D

Adsorption of water and carbon dioxide on hematite and consequences for possible hydrate formation

Bjørn Kvamme, Tatiana Kuznetsova, Pilvi-Helina Kivelæ

2012-01-09 Paper

DOI: 10.1039/C2CP23810A

Identification of a thermally activated process in the Cy3 photobleaching mechanism

A. L. Jouonang, P. Didier, Y. Mély

2011-12-21 Paper

DOI: 10.1039/C2CP22334A

You might also like

Compound Q&A

What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?

(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...

79066-03-8(3.beta.)-3-Hydroxy-...
Compound Q&A

What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?

5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...

89702-89-65-(aminomethyl)-2-me...
Compound Q&A

What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?

Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...

28981-13-7Thieno[2,3-c]pyridin...
Compound Q&A

Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?

1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...

1185311-28-71-[(6-Methoxy-3-pyri...
Compound Q&A

What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?

[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...

146404-58-2[(2E)-3-Phenyl-2-pro...
Compound Q&A

What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?

6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...

1620515-86-76-Bromo-7-methoxyqui...
Compound Q&A

What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?

This compound is primarily used in the pharmaceutical industry for the developme...

260550-89-8(2R)-1-(1-Benzofuran...
1228013-15-71-Ethyl-7-[2-methyl-...
Compound Q&A

Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?

Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...

1217500-78-1{5-(Acryloylamino)-2...
Compound Q&A

What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?

3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...

310881-48-23-(Piperidin-4-yloxy...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.