Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 50, Pages 11558-11564Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001368
Keywords
cyanation; DFT study; H-bonded template; para-C-H activation; regioselectivity
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Funding
- SERB India [CRG/2018/003951]
- National Natural Science Foundation of China [21973055]
- Natural Science Foundation of Shandong Province [ZR2019MB049]
- IITB-Monash Research Academy
- CSIR-India
- UGC
- DST-India [YSS/2014/000530]
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The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work, we demonstrate thepara-selective introduction of versatile nitrile moiety, enabled by a detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools, which heralds the inception ofpara-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.
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