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ACS Catalysis
Cross-Coupling of Aryl Phosphates with Grignard and Organo-
Carbonates, and Sulfamates. J. Am. Chem. Soc. 2009, 131, 17748; (b)
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. Suzuki-Miyaura Cross-Coupling of Aryl Carbamates
and Sulfamates: Experimental and Computational Studies. J. Am.
Chem. Soc. 2011, 133, 6352; (c) Leowanawat, P.; Zhang, N.;
Resmerita, A. M.; Rosen, B. M.; Percec, V. Ni(COD)2/PCy3 Catalyzed
Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with
Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room
Temperature. J. Org. Chem. 2011, 76, 9946; (d) Baghbanzadeh, M.;
Pilger, C.; Kappe, C. O. Rapid Nickel-Catalyzed Suzuki-Miyaura
Cross-Couplings of Aryl Carbamates and Sulfamates Utilizing
Microwave Heating. J. Org. Chem. 2011, 76, 1507; (e) Leowanawat,
P.; Zhang, N.; Safi, M.; Hoffman, D. J.; Fryberger, M. C.; George, A.;
Aluminum Reagents - Synthesis of Alkylbenzenes, Alkenylbenzenes
and Arylbenzenes from Phenols. Tetrahedron Lett. 1981, 22, 4449; (c)
Sengupta, S.; Leite, M.; Raslan, D. S.; Quesnelle, C.; Snieckus, V.
Ni(0)-Catalyzed Cross Coupling of Aryl O-Carbamates and Aryl
Triflates with Grignard Reagents - Directed Orthometallation-Aligned
Synthetic Methods for Polysubstituted Aromatics Via a 1,2-Dipole
Equivalent. J. Org. Chem. 1992, 57, 4066; (d) Dankwardt, J. W.
Nickel-catalyzed cross-coupling of aryl Grignard reagents with
aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls.
Angew. Chem. Int. Ed. 2004, 43, 2428; (e) Yu, D. G.; Li, B. J.; Zheng,
S. F.; Guan, B. T.; Wang, B. Q.; Shi, Z. J. Direct Application of
Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with
Aryl Grignard Reagents. Angew. Chem. Int. Ed. 2010, 49, 4566.
5. An isolated example of Ni-catalyzed cross coupling of a
pseudosaccharyl ether of naphthol with SnMe4 has been reported:
Brigas, A. F.; Johnstone, R. A. W. Heteroaromatic ethers of phenols in
nickel-catalysed ipso-replacement reactions with magnesium, zinc and
tin organometallic compounds. J. Chem. Soc., Perk. Trans. 1 2000,
1735.
6. Selected reviews: (a) Stille, J. K. The Palladium-Catalyzed Cross-
Coupling Reactions of Organotin Reagents with Organic Electrophiles.
Angew. Chem. Int. Ed. 1986, 25, 508; (b) Espinet, P.; Echavarren, A.
M. The mechanisms of the Stille reaction. Angew. Chem. Int. Ed. 2004,
43, 4704; (c) Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L. P. Stille
Polycondensation for Synthesis of Functional Materials. Chem. Rev.
2011, 111, 1493; (d) Heravi, M. M.; Hashemi, E.; Azimian, F. Recent
developments of the Stille reaction as a revolutionized method in total
synthesis. Tetrahedron 2014, 70, 7; (e) Cordovilla, C.; Bartolome, C.;
Martinez-Ilarduya, J. M.; Espinet, P. The Stille Reaction, 38 Years
Later. ACS Catal. 2015, 5, 3040.
7. Examples discussing the instability of some boronic acids: (a)
Tyrrell, E.; Brookes, P. The synthesis and applications of heterocyclic
boronic acids. Synthesis-Stuttgart 2003, 469; (b) Ge, S. Z.; Hartwig, J.
F. Highly Reactive, Single-Component Nickel Catalyst Precursor for
Suzuki-Miyuara Cross-Coupling of Heteroaryl Boronic Acids with
Heteroaryl Halides. Angew. Chem. Int. Ed. 2012, 51, 12837; (c) Cox,
P. A.; Leach, A. G.; Campbell, A. D.; Lloyd-Jones, G. C.
Protodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic
Acids: pH-Rate Profiles, Autocatalysis, and Disproportionation. J. Am.
Chem. Soc. 2016, 138, 9145; (d) Sawatzky, R. S.; Stradiotto, M.
(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging
Suzuki-Miyaura Cross-Couplings Leading to Unsymmetrical
Biheteroaryls. Synlett 2018, 29, 799.
8. Examples of alternative solutions to the instability of some
boronic acids: (a) Molander, G. A.; Ellis, N. Organotrifluoroborates:
Protected boronic acids that expand the versatility of the Suzuki
coupling reaction. Acc. Chem. Res. 2007, 40, 275; (b) Darses, S.; Genet,
J. P. Potassium organotrifluoroborates: New perspectives in organic
synthesis. Chem. Rev. 2008, 108, 288; (c) Dick, G. R.; Woerly, E. M.;
Burke, M. D. A General Solution for the 2-Pyridyl Problem. Angew.
Chem. Int. Ed. 2012, 51, 2667; (d) Knapp, D. M.; Gillis, E. P.; Burke,
M. D. A General Solution for Unstable Boronic Acids: Slow-Release
Cross-Coupling from Air-Stable MIDA Boronates. J. Am. Chem. Soc.
2009, 131, 6961; (e) Malapit, C. A.; Bour, J. R.; Brigham, C. E.;
Sanford, M. S. Base-free nickel-catalysed decarbonylative Suzuki-
Miyaura coupling of acid fluorides. Nature 2018, 563, 100.
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Percec,
V.
trans-Chloro(1-Naphthyl)bis(triphenylphosphine)-
nickel(II)/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl
Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and
Sulfamates at Room Temperature. J. Org. Chem. 2012, 77, 2885; (f)
Ramgren, S. D.; Hie, L.; Ye, Y. X.; Garg, N. K. Nickel-Catalyzed
Suzuki-Miyaura Couplings in Green Solvents. Org. Lett. 2013, 15,
3950; (g) Jezorek, R. L.; Zhang, N.; Leowanawat, P.; Bunner, M. H.;
Gutsche, N.; Pesti, A. K. R.; Olsen, J. T.; Percec, V. Air-Stable Nickel
Precatalysts for Fast and Quantitative Cross-Coupling of Aryl
Sulfamates with Aryl Neopentylglycolboronates at Room
Temperature. Org. Lett. 2014, 16, 6326.
12. (a) Littke, A. F.; Fu, G. C. The first general method for Stille
cross-couplings of aryl chlorides. Angew. Chem. Int. Ed. 1999, 38,
2411; (b) Grasa, G. A.; Nolan, S. P. Palladium/imidazolium salt
catalyzed coupling of aryl halides with hypervalent organostannates.
Org. Lett. 2001, 3, 119; (c) Martinez, A. G.; Barcina, J. O.; Heras, M.
D. C.; Cerezo, A. D. Reactions of vinyl and aryl triflates with
hypervalent tin reagents. Organometallics 2001, 20, 1020; (d) Littke,
A. F.; Schwarz, L.; Fu, G. C. Pd/P(t-Bu)3: A mild and general catalyst
for Stille reactions of aryl chlorides and aryl bromides. J. Am. Chem.
Soc. 2002, 124, 6343; (e) Su, W. P.; Urgaonkar, S.; McLaughlin, P. A.;
Verkade, J. G., Highly active palladium catalysts supported by bulky
proazaphosphatrane ligands for Stille cross-coupling: Coupling of aryl
and vinyl chlorides, room temperature coupling of aryl bromides,
coupling of aryl triflates, and synthesis of sterically hindered biaryls. J.
Am. Chem. Soc. 2004, 126, 16433; (f) Echavarren, A. M. Couplings
with monoorganotin compounds: A "radical" twist from the original
Stille reaction. Angew. Chem. Int. Edit. 2005, 44, 3962; (g) Naber, J.
R.; Buchwald, S. L., Palladium-catalyzed Stille cross-coupling reaction
of aryl chlorides using a pre-milled palladium acetate and XPhos
catalyst system. Adv. Synth. Catal. 2008, 350, 957; (h) Ariafard, A.;
Yates, B. F. Subtle Balance of Ligand Steric Effects in Stille
Transmetalation. J. Am. Chem. Soc. 2009, 131, 13981; (i) Herve, M.;
Lefevre, G.; Mitchell, E. A.; Maes, B. U. W.; Jutand, A. On the Triple
Role of Fluoride Ions in Palladium-Catalyzed Stille Reactions. Chem.
Eur. J. 2015, 21, 18401.
13. For use of fluoride in a Ni-catalyzed Stille coupling of Ar—
+
NMe3 electrophiles see: Wang, D. Y.; Kawahata, M.; Yang, Z. K.;
Miyamoto, K.; Komagawa, S.; Yamaguchi, K.; Wang, C.; Uchiyama,
M. Stille coupling via C—N bond cleavage. Nat. Commun. 2016, 7,
12937.
14. (a) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P.
Palladium-Catalyzed Coupling of Arylstannanes with Organic
Sulfonates - a Comprehensive Study. J. Org. Chem. 1993, 58, 5434; (b)
Casado, A. L.; Espinet, P.; Gallego, A. M. Mechanism of the Stille
reaction. 2. Couplings of aryl triflates with vinyltributyltin.
Observation of intermediates. A more comprehensive scheme. J. Am.
Chem. Soc. 2000, 122, 11771; (c) Verbeeck, S.; Meyers, C.; Franck, P.;
Jutand, A.; Maes, B. U. W. Dual Effect of Halides in the Stille
Reaction: In Situ Halide Metathesis and Catalyst Stabilization. Chem.
Eur. J. 2010, 16, 12831.
15. (a) Amii, H.; Uneyama, K. C—F Bond Activation in Organic
Synthesis. Chem. Rev. 2009, 109, 2119; (b) Tobisu, M.; Xu, T.;
Shimasaki, T.; Chatani, N. Nickel-Catalyzed Suzuki-Miyaura Reaction
of Aryl Fluorides. J. Am. Chem. Soc. 2011, 133, 19505.
16. (a) Bonesi, S. M.; Fagnoni, M. The Aromatic Carbon-Carbon
ipso-Substitution Reaction. Chem. Eur. J. 2010, 16, 13572; (b) Garcia,
9. (a) Badone, D.; Cecchi, R.; Guzzi, U. Palladium-Catalyzed
Coupling of Aryl Arenesulfonates with Organostannanes. J. Org.
Chem. 1992, 57, 6321; (b) Naber, J. R.; Fors, B. P.; Wu, X. X.; Gunn,
J. T.; Buchwald, S. L. Stille Cross-Coupling Reactions of Aryl
Mesylates and Tosylates Using a Biarylphosphine Based Catalyst
System. Heterocycles 2010, 80, 1215.
10. (a) Macklin, T. K.; Snieckus, V. Directed ortho metalation
methodology. The N,N-dialkyl aryl O-sulfamate as a new directed
metalation group and cross-coupling partner for Grignard reagents.
Org. Lett. 2005, 7, 2519; (b) Board, J.; Cosman, J. L.; Rantanen, T.;
Singh, S. P.; Snieckus, V., The Directed ortho Metallation-Cross-
Coupling Fusion: Development and Application in Synthesis Platinum
Metals Rev. 2013, 57, 234.
11. Examples: (a) Quasdorf, K. W.; Riener, M.; Petrova, K. V.;
Garg, N. K. Suzuki-Miyaura Coupling of Aryl Carbamates,
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