Synthesis of Conjugated Polymers by Sustainable Suzuki Polycondensation in Water and under Aerobic Conditions DOI Creative Commons
Alessandro Sanzone,

Adiel Calascibetta,

Mauro Monti

et al.

ACS Macro Letters, Journal Year: 2020, Volume and Issue: 9(8), P. 1167 - 1171

Published: July 31, 2020

Conjugated semiconducting polymers are key materials enabling plastic (opto)electronic devices. Research in the field has a generally strong focus on constant improvement of backbone structure and resulting properties. Comparatively fewer studies devoted to improving sustainability synthetic route that leads material under scrutiny. Exemplified by two established commercially available luminescent poly(9,9-dioctylfluorene-alt-bithiophene) (PF8T2) poly(9,9-dioctylfluorene-alt-benzothiadiazole) (PF8BT), this work describes first examples efficient Suzuki-Miyaura polycondensations water, ambient environment, with minimal amount organic solvent moderate heating. The approach enables reduction E-factor (mass waste/mass product) 1 order magnitude, without negatively affecting molecular weight, dispersity, chemical structure, or photochemical stability PF8T2 PF8BT.

Language: Английский

Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine‐Based Palladacycle DOI
Balaram S. Takale,

Ruchita R. Thakore,

Gianluca Casotti

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(8), P. 4158 - 4163

Published: Nov. 12, 2020

Abstract An inexpensive and new triphenylphosphine‐based palladacycle has been developed as a pre‐catalyst, leading to highly effective Stille cross‐coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving variety aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst aqueous nanoreactors formed by 2 wt % Brij‐30 water.

Language: Английский

Citations

39
An environmentally responsible 3-pot, 5-step synthesis of the antitumor agent sonidegib using ppm levels of Pd catalysis in water DOI
Balaram S. Takale,

Ruchita R. Thakore,

Fanyi Kong

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(23), P. 6258 - 6262

Published: Jan. 1, 2019

Sonidegib is a representative example of valued pharmaceutical prepared under environmentally responsible conditions.

Language: Английский

Citations

38
Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M DOI
Min Shi, Ning Ye, Wei Chen

et al.

Organic Process Research & Development, Journal Year: 2020, Volume and Issue: 24(8), P. 1543 - 1548

Published: Aug. 3, 2020

The technology of surfactant chemistry is employed for amide bond construction via the reaction acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling

Language: Английский

Citations

36
Sustainable and Cost-Effective Suzuki–Miyaura Couplings toward the Key Biaryl Subunits of Arylex and Rinskor Active DOI
Balaram S. Takale,

Ruchita R. Thakore,

Nicholas M. Irvine

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(12), P. 4823 - 4827

Published: June 10, 2020

Challenging Suzuki–Miyaura cross couplings associated with novel crop protection active ingredients from Corteva Agriscience, Arylex and Rinskor, can be performed in water using parts per million (ppm) levels of a Pd catalyst. Each coupling required distinct set reaction conditions to achieve maximum selectivities chemical yields. By way comparison, this chemistry is not only under environmentally responsible aqueous micellar conditions, but also involves lowering loadings (3–5 times) endangered palladium than used previously attain more sustainable process.

Language: Английский

Citations

33
Synthesis of Conjugated Polymers by Sustainable Suzuki Polycondensation in Water and under Aerobic Conditions DOI Creative Commons
Alessandro Sanzone,

Adiel Calascibetta,

Mauro Monti

et al.

ACS Macro Letters, Journal Year: 2020, Volume and Issue: 9(8), P. 1167 - 1171

Published: July 31, 2020

Conjugated semiconducting polymers are key materials enabling plastic (opto)electronic devices. Research in the field has a generally strong focus on constant improvement of backbone structure and resulting properties. Comparatively fewer studies devoted to improving sustainability synthetic route that leads material under scrutiny. Exemplified by two established commercially available luminescent poly(9,9-dioctylfluorene-alt-bithiophene) (PF8T2) poly(9,9-dioctylfluorene-alt-benzothiadiazole) (PF8BT), this work describes first examples efficient Suzuki-Miyaura polycondensations water, ambient environment, with minimal amount organic solvent moderate heating. The approach enables reduction E-factor (mass waste/mass product) 1 order magnitude, without negatively affecting molecular weight, dispersity, chemical structure, or photochemical stability PF8T2 PF8BT.

Language: Английский

Citations

33