Organic Letters
Letter
available, thus offering pursuit of considerable synthetic
Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg,
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N. K.; Percec, V. Chem. Rev. 2011, 111, 1346−1416. (c) For the
chemistry in the realm of aryl organophosphorus systems,
in particular, in the design and development of new ligands.
As in previous work from our laboratories, new directions
and applications for the construction of complex aromatic and
heteroaromatic frameworks, bioactive molecules, and natural
products within the combined DoM-cross coupling-DreM
conceptual framework may be uncovered.
7c
Suzuki−Miyaura reaction of ArOCONR , see: Quasdorf, K. W.;
2
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Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131,
1
7748−17749. Antoft-Finch, A.; Blackburn, T.; Snieckus, V. J. Am.
Chem. Soc. 2009, 131, 17750−17752. Quasdorf, K. W.; Antoft-Finch,
A.; Liu, P.; Silberstein, A. L.; Komaromi, A.; Blackburn, T.; Ramgren,
S. D.; Houk, K. N.; Snieckus, V.; Garg, N. K. J. Am. Chem. Soc. 2011,
1
33, 6352−6363. (d) For recent reviews on various DG directed C−
H functionalization, see: Huang, Z.; Lim, H. N.; Mo, F.; Young, M.
C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764−7786. Gensch, T.;
Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev.
ASSOCIATED CONTENT
sı Supporting Information
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*
2
016, 45, 2900−2936. Zhao, Q.; Poisson, T.; Pannecoucke, X.;
Besset, T. Synthesis 2018, 49, 4808−4826.
4) The Ni-catalyzed Suzuki−Miyaura cross coupling of phenyl and
(
1
naphthyl O-phosphoro bis(2-oxo-3-oxazolidinyl)diamides has been
reported: Zhao, Y.-L.; Li, Y.; Li, Y.; Gan, L.-X.; Han, F.-S. Chem. - Eur.
J. 2010, 16, 4991−4994.
(5) (a) For a highlight, see: Tobisu, M.; Chatani, N. Angew. Chem.,
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Int. Ed. 2009, 48, 3565−3568. (b) For recent work, see: Muto, K.;
Yamaguchi, J.; Musaev, D. G.; Itami, K. Nat. Commun. 2015, 6,
7508−7516.
(6) (a) For the anionic ortho Fries rearrangement reaction, see: Sibi,
M.; Snieckus, V. J. Org. Chem. 1983, 48, 1935−1937. (b) For the
analogous DreM reaction of biaryl O-carbamates, see: Wang, X.;
Snieckus, V. Tetrahedron Lett. 1991, 32, 4879−4882. (c) For a
review, see: Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew.
Chem., Int. Ed. 2004, 43, 2206−2225. (d) For a recent excellent
review, see: Korb, M.; Lang, H. Chem. Soc. Rev. 2019, 48, 2829−2882.
Jignesh J. Patel − Department of Chemistry, Queen’s University,
Kingston K7L 3N6, ON, Canada
Thomas Blackburn − Department of Chemistry, Queen’s
University, Kingston K7L 3N6, ON, Canada
Manlio Alessi − Department of Chemistry, Queen’s University,
Kingston K7L 3N6, ON, Canada
(7) (a) For general reviews on Buchwald’s phosphine ligands, see:
Mauger, C. C.; Mignani, G. A. Aldrichimica Acta 2006, 39, 17.
Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599−1626.
Martin, R.; Buchwald, S. Acc. Chem. Res. 2008, 41, 1461−1473.
Ingoglia, B. T.; Wagen, C. C.; Buchwald, S. L. Tetrahedron 2019, 75,
4199−4211. Forero-Cortes, P. A.; Haydl, A. M. Org. Process Res. Dev.
Hannah Sawinski − Department of Chemistry, Queen’s
University, Kingston K7L 3N6, ON, Canada
2019, 23, 1478−1483. (b) For BINOLs in asymmetric catalysis, see:
Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155−3212.
Brunel, J. M. Chem. Rev. 2005, 105, 857−898. (c) For chiral
phosphoric acid BINOLs, see: Parmar, D.; Sugiono, E.; Raja, S.;
Rueping, M. Chem. Rev. 2014, 114, 9047−9153.
Notes
(
4
(
1
8) Lennox, A. J. J.; Lloyd-Jones, G. C. Chem. Soc. Rev. 2014, 43,
12−443.
9) Puumala, K. A., M.Sc. Thesis, University of Waterloo, Canada,
997.
10) (a) Aryl phosphates: Hayashi, T.; Katsuro, Y.; Okamoto, Y.;
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We are grateful to NSERC for support under the Discovery
Grant program and to Dr. Franco
■
(
̧
ise Sauriol (Department of
Kumada, M. Tetrahedron Lett. 1981, 22, 4449−4452. (b) Vinyl
phosphates: Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980,
21, 2531−2534. Fuwa, H.; Sasaki, M. Org. Lett. 2007, 9, 3347−3350.
(c) Alkenyl phosphates: Hansen, A. L.; Ebran, J.-P.; Gøgsig, T. M.;
Skrydstrup, T. J. Org. Chem. 2007, 72, 6464−6472. (d) For reductive
cleavage, see: Lepifre, F.; Clavier, S.; Bouyssou, P.; Coudert, G.
Tetrahedron 2001, 57, 6969−6975. (e) For an application in natural
product synthesis, see: Huang, W. G.; Jiang, Y. Y.; Li, Q.; Li, J.; Li, J.
Y.; Lu, W.; Cai, J. C. Tetrahedron 2005, 61, 1863−1870.
Chemistry, Queen’s University) for NMR expertise. We are
thankful to Mr. James Frendo-Cumbo (Department of
Chemistry, Queen’s University) for his help in some
experimental work.
DEDICATION
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In memory of Dieter Enders for his immediately recognized
SAMP and RAMP reagents, for caring mentorship of students,
and for altruism in all forms of interaction.
(
11) Hansen, A. L.; Ebran, J.-P.; Gogsig, T. M.; Skrydstrup, T. Chem.
Commun. 2006, 4137−4139.
12) Although these conditions appear to be adequate, given the
(
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(
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