Platinum Catalysis Revisited—Unraveling Principles of Catalytic Olefin Hydrosilylation

ACS Catalysis ◽  
2016 ◽  
Vol 6 (2) ◽  
pp. 1274-1284 ◽  
Author(s):  
Teresa K. Meister ◽  
Korbinian Riener ◽  
Peter Gigler ◽  
Jürgen Stohrer ◽  
Wolfgang A. Herrmann ◽  
...  
Keyword(s):  



1987 ◽  
Vol 29 (2) ◽  
pp. 193-201 ◽  
Author(s):  
G.C. Georgiades ◽  
S.J. McCarthy ◽  
P.A. Sermon
Keyword(s):  


2019 ◽  
Vol 5 (12) ◽  
pp. eaay1537 ◽  
Author(s):  
Cuibo Liu ◽  
Zhongxin Chen ◽  
Huan Yan ◽  
Shibo Xi ◽  
Kah Meng Yam ◽  
...  

Unprotected E-hydrazone esters are prized building blocks for the preparation of 1H-indazoles and countless other N-containing biologically active molecules. Despite previous advances, efficient and stereoselective synthesis of these compounds remains nontrivial. Here, we show that Pt single atoms anchored on defect-rich CeO2 nanorods (Pt1/CeO2), in conjunction with the alcoholysis of ammonia borane, promotes exceptionally E-selective hydrogenation of α-diazoesters to afford a wide assortment of N-H hydrazone esters with an overall turnover frequency of up to 566 hours−1 upon reaction completion. The α-diazoester substrates could be generated in situ from readily available carboxylic esters in one-pot hydrogenation reaction. Utility is demonstrated through concise, scalable synthesis of 1H-indazole–derived pharmaceuticals and their 15N-labeled analogs. The present protocol highlights a key mechanistic nuance wherein simultaneous coordination of a Pt site with the diazo N═N and ester carbonyl motifs plays a central role in controlling stereoselectivity, which is supported by density functional theory calculations.



2017 ◽  
Vol 65 (2) ◽  
pp. 41-46
Author(s):  
Toru TSUKANO ◽  
Daisuke MAEDA ◽  
Yousuke SASAYAMA ◽  
Daisuke NAKATA ◽  
Masatoshi SUGIOKA ◽  
...  






2016 ◽  
Vol 129 (2) ◽  
pp. 620-624 ◽  
Author(s):  
Wen-Bo Shen ◽  
Xin-Yu Xiao ◽  
Qing Sun ◽  
Bo Zhou ◽  
Xin-Qi Zhu ◽  
...  


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