TY - JOUR
T1 - Site-selective and metal-free C-H phosphonation of arenes via photoactivation of thianthrenium salts
AU - Gallego-Gamo, Albert
AU - Reyes-Mesa, David
AU - Guinart-Guillem, Axel
AU - Pleixats, Roser
AU - Gimbert-Suriñach, Carolina
AU - Vallribera, Adelina
AU - Granados, Albert
N1 - Publisher Copyright:
© 2023 The Royal Society of Chemistry.
PY - 2023/8/8
Y1 - 2023/8/8
N2 - Aryl phosphonates are prevalent moieties in medicinal chemistry and agrochemicals. Their chemical synthesis normally relies on the use of precious metals, harsh conditions or aryl halides as substrates. Herein, we describe a sustainable light-promoted and site-selective C-H phosphonation of arenes via thianthrenation and the formation of an electron donor-acceptor complex (EDA) as key steps. The method tolerates a wide range of functional groups including biomolecules. The use of sunlight also promotes this transformation and our mechanistic investigations support a radical chain mechanism.
AB - Aryl phosphonates are prevalent moieties in medicinal chemistry and agrochemicals. Their chemical synthesis normally relies on the use of precious metals, harsh conditions or aryl halides as substrates. Herein, we describe a sustainable light-promoted and site-selective C-H phosphonation of arenes via thianthrenation and the formation of an electron donor-acceptor complex (EDA) as key steps. The method tolerates a wide range of functional groups including biomolecules. The use of sunlight also promotes this transformation and our mechanistic investigations support a radical chain mechanism.
UR - http://www.scopus.com/inward/record.url?scp=85170572730&partnerID=8YFLogxK
U2 - 10.1039/d3ra04512a
DO - 10.1039/d3ra04512a
M3 - Article
C2 - 37559697
AN - SCOPUS:85170572730
SN - 2046-2069
VL - 13
SP - 23359
EP - 23364
JO - RSC ADVANCES
JF - RSC ADVANCES
IS - 33
ER -