TY  - JOUR
A1  - Wessig, Pablo
A1  - Krebs, Saskia
T1  - N-aroylsulfonamide-photofragmentation (ASAP)
BT  - a versatile route to biaryls
JF  - European journal of organic chemistry
N2  - The photochemical fragmentation of N-aroylsulfonamides 9 (ASAP) is a powerful method for the preparation of various biaryls. Compounds 9 are easily accessible in two steps from amines by treatment with arenesulfonyl chlorides and aroyl chlorides. Many of these compounds were prepared for the first time. The irradiation takes place in a previously developed continuous-flow reactor using inexpensive UVB or UVC fluorescent lamps. Isocyanates and sulphur dioxide are formed as the only by-products. The ASAP tolerates a variety of functional groups and is even suited for the preparation of phenylnaphthalenes and terphenyls. The ASAP mechanism was elucidated by interaction of photophysical and quantum chemical (DFT) methods and revealed a spirocyclic biradical as key intermediate.
KW  - Biaryls
KW  - Fragmentation
KW  - Isocyanates
KW  - Photochemistry
KW  - Sulfonamides
Y1  - 2021
U6  - https://doi.org/10.1002/ejoc.202100955
SN  - 1434-193X
SN  - 1099-0690
VL  - 2021
IS  - 46
SP  - 6367
EP  - 6374
PB  - Wiley-VCH
CY  - Weinheim
ER  -