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

Synthesis and characterization of poly(ethene–ketone–arylene–ketone)s containing pendant methylthio groups via metal-free catalyzed copolymerization of aryldiynes with DMSO

Weiqiang Fu, Lichao Dong, Jianbing Shi, Bin Tong, Zhengxu Cai, Junge Zhi, Yuping Dong

2018-07-31 Paper

DOI: 10.1039/C8PY00819A

Correction: The effects of polymer topology and chain length on the antimicrobial activity and hemocompatibility of amphiphilic ternary copolymers

Rashin Namivandi-Zangeneh, Rebecca J. Kwan, Thuy-Khanh Nguyen, Jonathan Yeow, Frances L. Byrne, Edgar H. H. Wong, Cyrille Boyer

2017-09-11 Correction

DOI: 10.1039/C7PY90140B

Highly efficient access to well-defined linear polymers with substantial vinyl pendants via ATRP of divinyl monomers

Xiao-Yan Wang, Xiu-Li Sun, Zhi-Hao Chen, Feng Wang, Sunewang R. Wang, Yong Tang

2018-07-26 Paper

DOI: 10.1039/C8PY00797G

Swelling properties of thermoresponsive/hydrophilic co-networks with functional crosslinked domain structures

Shohei Ida, Hironobu Kitanaka, Tatsuya Ishikawa, Shokyoku Kanaoka, Yoshitsugu Hirokawa

2018-01-03 Paper

DOI: 10.1039/C7PY01793F

Regioselective living polymerization of allylcyclohexane and precise synthesis of hydrocarbon block copolymers with cyclic units

Jie Gao, Zonghang Ying, Liu Zhong, Heng Liao, Haiyang Gao, Wu Qing

2018-02-07 Paper

DOI: 10.1039/C8PY00047F

Hyperbranched polysiloxane with highly constrained rings and the effect of the attached arms on the assembly behavior

Chunyan Wu, Chunhua Hu, Yuzhou Liu

2017-10-06 Communication

DOI: 10.1039/C7PY01177F

Inhibition of lysozyme's polymerization activity using a polymer structural mimic

D. L. Morris, T. C. Leeper, C. J. Ziegler

2018-05-29 Communication

DOI: 10.1039/C8PY00545A

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 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.