Solid-state cross-coupling reactions of insoluble aryl halides under polymer-assisted grinding conditions

Koji Kubota; Tamae Seo; Hajime Ito

doi:10.1039/d2fd00121g

journal article Jan 01, 2023

Solid-state cross-coupling reactions of insoluble aryl halides under polymer-assisted grinding conditions

Koji Kubota

Tamae Seo Hajime Ito

Faraday Discussions Vol. 241 pp. 104-113 · Royal Society of Chemistry (RSC)

View at Publisher Save 10.1039/d2fd00121g

Abstract

The efficiency of challenging solid-state cross-coupling of insoluble aryl halides was improved by the addition of polytetrafluoroethylene (PTFE) as a POLAG additive under high-temperature ball-milling conditions.

Topics

No keywords indexed for this article. Browse by subject →

References

65

[1]

James Chem. Soc. Rev. (2012) 10.1039/c1cs15171a

[2]

Wang Chem. Soc. Rev. (2013) 10.1039/c3cs35526h

[3]

Do ACS Cent. Sci. (2017) 10.1021/acscentsci.6b00277

[4]

Hernández J. Org. Chem. (2017) 10.1021/acs.joc.6b02887

[5]

Hernández Chem.–Eur. J. (2017) 10.1002/chem.201703605

[6]

Achar Beilstein J. Org. Chem. (2017) 10.3762/bjoc.13.186

[7]

Do Synlett (2017) 10.1055/s-0036-1590854

[8]

Tan Eur. J. Org. Chem. (2018) 10.1002/ejoc.201700961

[9]

Mechanochemistry as an emerging tool for molecular synthesis: what can it offer?

Joseph L. Howard, Qun Cao, Duncan L. Browne

Chemical Science 2018 10.1039/c7sc05371a

[10]

Mechanochemistry and organic synthesis: from mystical to practical

J. Andersen, J. Mack

Green Chem. 2018 10.1039/c7gc03797j

[11]

Rightmire Dalton Trans. (2016) 10.1039/c5dt03866a

[12]

Leonardi Chem. Sci. (2018) 10.1039/c7sc05370c

[13]

Tan Chem. Commun. (2016) 10.1039/c6cc02015a

[14]

Tan Chem. Soc. Rev. (2019) 10.1039/c7cs00813a

[15]

Bolm Angew. Chem., Int. Ed. (2019) 10.1002/anie.201810902

[16]

Friščić Angew. Chem., Int. Ed. (2020) 10.1002/anie.201906755

[17]

Kubota Trends Chem. (2020) 10.1016/j.trechm.2020.09.006

[18]

Egorov Green Chem. (2020) 10.1039/c9gc03414e

[19]

Porcheddu ACS Catal. (2020) 10.1021/acscatal.0c00142

[20]

Ying Adv. Synth. Catal. (2021) 10.1002/adsc.202001245

[21]

Ardila-Fierro ChemSusChem (2021) 10.1002/cssc.202100478

[22]

K.Tanaka , Solvent-Free Organic Synthesis , Wiley-VCH , Weinheim , 2nd edn, 2009

[23]

F.Toda , Organic Solid-State Reactions , Springer , Berlin Heidelberg , 2004

[24]

Toda Acc. Chem. Res. (1995) 10.1021/ar00060a003

[25]

Tanaka Chem. Rev. (2000) 10.1021/cr940089p

[26]

Redox reactions of small organic molecules using ball milling and piezoelectric materials

Koji Kubota, Yadong Pang, Akira Miura et al.

Science 2019 10.1126/science.aay8224

[27]

Kubota Chem. Sci. (2019) 10.1039/c9sc01711a

[28]

Kubota Nat. Commun. (2019) 10.1038/s41467-018-08017-9

[29]

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

Tamae Seo, Naoki Toyoshima, Koji Kubota et al.

Journal of the American Chemical Society 2021 10.1021/jacs.1c00906

[30]

Pang Angew. Chem., Int. Ed. (2020) 10.1002/anie.202009844

[31]

Kubota Angew. Chem., Int. Ed. (2021) 10.1002/anie.202105381

[32]

Takahashi Nat. Commun. (2021) 10.1038/s41467-021-26962-w

[33]

Kubota Synlett (2022) 10.1055/a-1748-3797

[34]

Báti Angew. Chem., Int. Ed. (2020) 10.1002/anie.202007815

[35]

Nielsen Synth. Commun. (2000) 10.1080/00397910008087262

[36]

Klingensmith Tetrahedron Lett. (2003) 10.1016/s0040-4039(02)02645-x

[37]

Bernhardt Beilstein J. Org. Chem. (2010) 10.3762/bjoc.6.7

[38]

Schneider Green Chem. (2009) 10.1039/b915744c

[39]

Schneider Org. Process Res. Dev. (2009) 10.1021/op800148y

[40]

The role of solvent in mechanochemical and sonochemical cocrystal formation: a solubility-based approach for predicting cocrystallisation outcome

Tomislav Friščić, Scott L. Childs, Syed A. A. Rizvi et al.

CrystEngComm 2009 10.1039/b815174a

[41]

Friščić Angew. Chem., Int. Ed. (2010) 10.1002/anie.200906583

[42]

Ying Adv. Synth. Catal. (2021) 10.1002/adsc.202001245

[43]

Jiang J. Org. Chem. (2016) 10.1021/acs.joc.6b01938

[44]

Mascitti Beilstein J. Org. Chem. (2017) 10.3762/bjoc.13.3

[45]

Hasa Angew. Chem., Int. Ed. (2015) 10.1002/ange.201501638

[46]

Hasa Cryst. Growth Des. (2016) 10.1021/acs.cgd.6b00084

[47]

Scaramuzza Cryst. Growth Des. (2018) 10.1021/acs.cgd.8b00687

[48]

Declerck Chem. Commun. (2012) 10.1039/c2cc36286d

[49]

Li Compos. Sci. Technol. (2020) 10.1016/j.compscitech.2020.108197

[50]

Sari Energy Build. (2018) 10.1016/j.enbuild.2018.01.009

Showing 50 of 65 references

Metrics

28

Citations

65

References

Details

Published: Jan 01, 2023
Vol/Issue: 241
Pages: 104-113
License: View

Authors

K

Koji Kubota

Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido, Japan; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido, Japan

T

Tamae Seo

Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido, Japan

H

Hajime Ito

Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido, Japan; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido, Japan

Funding

Japan Society for the Promotion of Science Award: 21H01926

Ministry of Education, Culture, Sports, Science and Technology

Japan Science and Technology Agency Award: PJ2521A02I

Core Research for Evolutional Science and Technology Award: JPMJCR19R1

Cite This Article

Koji Kubota, Tamae Seo, Hajime Ito (2023). Solid-state cross-coupling reactions of insoluble aryl halides under polymer-assisted grinding conditions. Faraday Discussions, 241, 104-113. https://doi.org/10.1039/d2fd00121g

Solid-state cross-coupling reactions of insoluble aryl halides under polymer-assisted grinding conditions

You May Also Like