- Photocatalyzed borylation using water-soluble quantum dots
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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.
- Chandrashekar, Hediyala B.,Maji, Arun,Halder, Ganga,Banerjee, Sucheta,Bhattacharyya, Sayan,Maiti, Debabrata
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Read Online
- Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes
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A Cu-catalyzed method has been identified for selective oxidative arylation of benzylic C-H bonds with arylboronic esters. The resulting 1,1-diarylalkanes are accessed directly from inexpensive alkylarenes containing primary and secondary benzylic C-H bonds, such as toluene or ethylbenzene. All catalyst components are commercially available at low cost, and the arylboronic esters are either commercially available or easily accessible from the commercially available boronic acids. The potential utility of these methods in medicinal chemistry applications is highlighted.
- Vasilopoulos, Aristidis,Zultanski, Susan L.,Stahl, Shannon S.
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supporting information
p. 7705 - 7708
(2017/06/20)
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- Improved preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane and its use in a simple [PdCl2(TPP)2]-catalyzed borylation of aryl bromides and iodides
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We describe a convenient preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane (MethylPentaneDiolBorane, MPBH) and demonstrate that it is an excellent reagent for the [PdCl2(PPh3)2]-catalyzed borylation of aryl bromides and iodides. The corresponding boronic esters undergo rapid Suzuki coupling reactions in the presence of cesium fluoride. Thus, MPBH is an excellent alternative to pinacolborane for Pd-catalyzed borylation and cross-coupling reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- PraveenGanesh, Nageswaran,Chavant, Pierre Yves
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experimental part
p. 4690 - 4696
(2009/05/27)
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