Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted
Aryl Azides To Access Medium-Sized N‑Heterocycles
Posted on 2017-03-29 - 20:04
A new reactivity pattern of Rh2(II)-N-arylnitrenes was discovered that facilitates
the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted
aryl azides. The key ring-expansion step of the catalytic cycle is
both chemoselective and stereospecific. Our mechanistic
experiments implicate the formation of a rhodium N-arylnitrene catalytic intermediate and reveal that sp3 C–H bond amination of this electrophilic species is competitive
with the ring-expansion process.
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Mazumdar, Wrickban; Jana, Navendu; Thurman, Bryant T.; Wink, Donald J.; Driver, Tom G. (2017). Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted
Aryl Azides To Access Medium-Sized N‑Heterocycles. ACS Publications. Collection. https://doi.org/10.1021/jacs.7b01833
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AUTHORS (5)
WM
Wrickban Mazumdar
NJ
Navendu Jana
BT
Bryant T. Thurman
DW
Donald J. Wink
TD
Tom G. Driver