In summary, we have successfully developed a Mn(III)-
mediated regioselective phosphonation reaction of arylalkenes
bearing conjugated groups such as ketone, amide, nitro, or
ester at the a-position. The reactions are straightforward and
highly efficient. The reactions can be used for arylalkynes to
prepare 1H-inden-1-one derivatives. Since the intermediate
carbon radical has the tendency to undergo rearrangement,
this reaction process could be further developed for making
more complicated ring systems bearing the dialkylphosphonyl
functionality.
JPZ thanks the National Natural Science Foundation of
China for financial support (No. 20772088).
Notes and references
Scheme 3 Phosphonation of a conjugated arylalkyne.
Table 3 Phosphonation of conjugated alkynes
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3
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16 Crystal
data
for
C11H14NO4P, M = 255.21, monoclinic, a = 24.732(4) A, b =
(E)-3-phenyl-2-phosphonylacrylamide
produced mixtures of regio- and E/Z isomers of hydro-
phosphonation products.
9.2832(11) A, c = 18.052(3) A, b = 105.924(4)1, U = 3985.5(9) A3,
T = 293 K, space group P 21/c, Z = 12, Dc = 1.276 g cmÀ3
Nonius Kappa CCD diffractometer, m(Mo-Ka) = 0.209 mmÀ1
,
,
37451 independent reflections (7277 observed), 466 parameters,
Rint = 0.0649, R = 0.0837, wR(F2) = 0.1495, thermal ellipsoids
probability level is 20%. CCDC 743887.
ꢀc
This journal is The Royal Society of Chemistry 2010
Chem. Commun., 2010, 46, 1721–1723 | 1723