Photocatalyzed borylation using water-soluble quantum dots

Hediyala B. Chandrashekar; Arun Maji; Ganga Halder; Sucheta Banerjee; Sayan Bhattacharyya; Debabrata Maiti

doi:10.1039/c9cc01737b

Photocatalyzed borylation using water-soluble quantum dots

Hediyala B. Chandrashekar
, Arun Maji
, Ganga Halder
, Sucheta Banerjee
, Sayan Bhattacharyya
, Debabrata Maiti

Pharmaceutical Sciences

Producción científica: Article › revisión exhaustiva

44 Citas (Scopus)

Resumen

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Idioma original	English
Páginas (desde-hasta)	6201-6204
Número de páginas	4
Publicación	Chemical Communications
Volumen	55
N.º	44
DOI	https://doi.org/10.1039/c9cc01737b
Estado	Published - 2019

Nota bibliográfica

Publisher Copyright:
© 2019 The Royal Society of Chemistry.

Financiación

This activity is supported by SERB (CRG/2018/003951) for D. M. and SERB (EMR/2016/001703) for S. B. Fellowship support for C. H. B, S. B. & G. H. (UGC) A. M. (CSIR), are humbly acknowledged. D. M. acknowledges Prof. Anindya Datta for femtosecond pump-probe spectroscopy setup.

Financiadores	Número del financiador
Council of Scientific and Industrial Research, India
Research Grants Council, University Grants Committee
Science and Engineering Research Board	EMR/2016/001703, CRG/2018/003951

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Acceder al documento

10.1039/c9cc01737b

Otros archivos y enlaces

Citar esto

@article{4881793c11124b1197e85392261eeddd,

title = "Photocatalyzed borylation using water-soluble quantum dots",

abstract = "The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.",

author = "Chandrashekar, \{Hediyala B.\} and Arun Maji and Ganga Halder and Sucheta Banerjee and Sayan Bhattacharyya and Debabrata Maiti",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c9cc01737b",

language = "English",

volume = "55",

pages = "6201--6204",

number = "44",

}

TY - JOUR

T1 - Photocatalyzed borylation using water-soluble quantum dots

AU - Chandrashekar, Hediyala B.

AU - Maji, Arun

AU - Halder, Ganga

AU - Banerjee, Sucheta

AU - Bhattacharyya, Sayan

AU - Maiti, Debabrata

PY - 2019

Y1 - 2019

N2 - The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

AB - The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

UR - https://www.scopus.com/pages/publications/85066454349

UR - https://www.scopus.com/pages/publications/85066454349#tab=citedBy

U2 - 10.1039/c9cc01737b

DO - 10.1039/c9cc01737b

M3 - Article

C2 - 31073563

AN - SCOPUS:85066454349

SN - 1359-7345

VL - 55

SP - 6201

EP - 6204

JO - Chemical Communications

JF - Chemical Communications

IS - 44

ER -

Photocatalyzed borylation using water-soluble quantum dots

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

Acceder al documento

Otros archivos y enlaces

Huella

Citar esto