TY - JOUR
T1 - Development of a General Organophosphorus Radical Trap
T2 - Deoxyphosphonylation of Alcohols
AU - Bissonnette, Noah B.
AU - Bisballe, Niels
AU - Tran, Andrew V.
AU - Rossi-Ashton, James A.
AU - MacMillan, David W.C.
N1 - Publisher Copyright: © 2024 American Chemical Society
PY - 2024/3/27
Y1 - 2024/3/27
N2 - Here we report the design of a general, redox-switchable organophosphorus alkyl radical trap that enables the synthesis of a broad range of C(sp3)-P(V) modalities. This “plug-and-play” approach relies upon in situ activation of alcohols and O═P(R2)H motifs, two broadly available and inexpensive sources of molecular complexity. The mild, photocatalytic deoxygenative strategy described herein allows for the direct conversion of sugars, nucleosides, and complex pharmaceutical architectures to their organophosphorus analogs. This includes the facile incorporation of medicinally relevant phosphonate ester prodrugs.
AB - Here we report the design of a general, redox-switchable organophosphorus alkyl radical trap that enables the synthesis of a broad range of C(sp3)-P(V) modalities. This “plug-and-play” approach relies upon in situ activation of alcohols and O═P(R2)H motifs, two broadly available and inexpensive sources of molecular complexity. The mild, photocatalytic deoxygenative strategy described herein allows for the direct conversion of sugars, nucleosides, and complex pharmaceutical architectures to their organophosphorus analogs. This includes the facile incorporation of medicinally relevant phosphonate ester prodrugs.
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U2 - 10.1021/jacs.4c00557
DO - 10.1021/jacs.4c00557
M3 - Article
C2 - 38470101
SN - 0002-7863
VL - 146
SP - 7942
EP - 7949
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 12
ER -