- Benzoic Acid-Promoted C2-H Borylation of Indoles with Pinacolborane
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A benzoic acid-promoted C2-H borylation of indoles with pinacolborane to afford C2-borylated indoles is developed. Preliminary mechanistic studies indicate BH3-related borane species formed via the decomposition of pinacolborane to be the probable catalyst. This transformation provides a prompt route toward the synthesis of diverse C2-functionalized indoles.
- Zou, Youliang,Zhang, Binfeng,Wang, Li,Zhang, Hua
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supporting information
p. 2821 - 2825
(2021/04/13)
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- C-H borylation by platinum catalysis
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Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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p. 332 - 342
(2017/05/09)
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- C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
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Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 12211 - 12214
(2015/10/12)
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- Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex
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An efficient, regioselective synthesis of fluorine-substituted arylboronic esters was achieved through fluorine-controlled C-H borylation of arenes with diboron catalyzed by a PSiN-platinum complex. The promising utility of the PSiN-platinum catalyst and its unique regioselectivity were demonstrated for the first time, which would complement the well-developed Ir-catalyzed C-H borylation.
- Takaya, Jun,Ito, Shisei,Nomoto, Hironori,Saito, Narumasa,Kirai, Naohiro,Iwasawa, Nobuharu
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supporting information
p. 17662 - 17665
(2015/12/18)
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