AUTHOR=Satkar Yuvraj , Wrobel Kazimierz , Trujillo-González Daniel E. , Ortiz-Alvarado Rafael , Jiménez-Halla J. Oscar C. , Solorio-Alvarado César R. 

TITLE=The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols

JOURNAL=Frontiers in Chemistry

VOLUME=8

YEAR=2020

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2020.563470

DOI=10.3389/fchem.2020.563470

ISSN=2296-2646

ABSTRACT=<p>The chemoselective reaction of the <italic>C</italic>- followed by the <italic>O-</italic>centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential <inline-formula><mml:math id="M1" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msubsup><mml:mtext>C</mml:mtext><mml:mrow><mml:mi>s</mml:mi><mml:mi>p</mml:mi></mml:mrow><mml:mn>2</mml:mn></mml:msubsup></mml:mrow></mml:math></inline-formula>-<inline-formula><mml:math id="M2" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msubsup><mml:mtext>C</mml:mtext><mml:mrow><mml:mi>s</mml:mi><mml:mi>p</mml:mi></mml:mrow><mml:mn>2</mml:mn></mml:msubsup></mml:mrow></mml:math></inline-formula>/O-<inline-formula><mml:math id="M3" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msubsup><mml:mtext>C</mml:mtext><mml:mrow><mml:mi>s</mml:mi><mml:mi>p</mml:mi></mml:mrow><mml:mn>2</mml:mn></mml:msubsup></mml:mrow></mml:math></inline-formula> bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMP<sub>2</sub>O. Experimental and DFT calculations provided a complete panorama of the reaction mechanism.</p>