Journal of the American Chemical Society
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5.
For the enantioselective cross-coupling, see: (a) Woods, B.
Notes
The authors declare no competing financial interests.
P.; Orlandi, M.; Huang, C.-Y.; Sigman, M.-S. Doyle, A. G.
Nickel-Catalyzed Enantioselective Reductive Cross-
Coupling of Styrenyl Aziridines. J. Am. Chem. Soc. 2017, 139,
5688–5691. (b) Poremba, K. E.; Kadunce, N. T.; Suzuki, N.;
Cherney, A. H.; Reisman, S. E. Nickel-Catalyzed Asymmet-
ric Reductive Cross-Coupling To Access 1,1-Diarylalkanes. J.
Am. Chem. Soc. 2017, 139, 5684–5687. (c) Ackerman, L. K.
G.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Cobalt
co-catalysis for cross-electrophile coupling: diarylmethanes
from benzyl mesylates and aryl halides. Chem. Sci. 2015, 6,
1115. (d) Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander,
G. A.; Kozlowski, M. C. Nickel-Catalyzed Cross-Coupling of
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ACKNOWLEDGMENT
This work was financially supported by the Strategic Priority
Research Program of the Chinese Academy of Sciences
(Grant XDB20000000), “1000-Youth Talents Plan”, NSF of
China (Grant 21572245, 21772222, 21772220), and S&TCSM of
Shanghai (Grant 17JC1401200, 18JC1415600).
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REFERENCES
Photoredox-Generated Radicals: Uncovering
a General
Manifold for Stereoconvergence in Nickel-Catalyzed Cross-
Couplings. J. Am. Chem. Soc. 2015, 137, 4896–4899. (e) Tel-
lis, J. C.; Primer, D. N.; Molander, G. A. Single-electron
transmetalation in organoboron cross-coupling by photo-
redox/nickel dual catalysis. Science 2014, 345, 433–436. (f)
Do, H.-Q.; Chandrashekar, E. R. R.; Fu, G. C. Nick-
el/Bis(Oxazoline)-Catalyzed Asymmetric Negishi Aryla-
tions of Racemic Secondary Benzylic Electrophiles to
Genrate Enantioenriched 1,1-Diarylalkanes. J. Am. Chem.
Soc. 2013, 135, 16288–16291.
For selected examples on the stereospecific cross-couplings,
see: (a) Rygus, J. P. G.; Crudden, C. M. Enantiospecific and
Iterative Suzuki-Miyaora Cross-Couplings. J. Am. Chem.
Soc. 2017, 139, 18124–18137. (b) Zhou, Q.; Srinivas, H. D.;
Dasgupta, S.; Watson, M. P. Nickel-Catalyzed Cross-
Couplings of Benzylic Pivalates with Arylboroxines: Stereo-
specific Formation of Diarylalkanes and Triarylmethanes. J.
Am. Chem. Soc. 2013, 135, 3307–3310. (c) Taylor, B. L. H.;
Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. Stereospecific Nick-
el-Catalyzed Cross-Coupling Reactions of Alkyl Ethers: En-
antioselective Synthesis of Diarylethanes. J. Am. Chem. Soc.
2011, 133, 389–391. (d) He, A.; Falck, J. R. Stereospecific Su-
zuki Cross-Coupling of Alkyl -Cyanohydrin Triflates. J.
Am. Chem. Soc. 2010, 132, 2524–2525. (f) López-Pérez, A.;
Adrio, J.; Carretero, J. C. Palladium-Catalyzed Cross-
Coupling Reaction of Secondary Benzylic Bromides with
Grignard Reagents. Org. Lett. 2009, 11, 5514–5517. (g) Imao,
D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. Cross
Coupling Reactions of Chiral Secondary Organoboronic Es-
ters With Retention of Configuration. J. Am. Chem. Soc.
2009, 131, 5024–5025.
For selected examples, see: (a) Grélaud, S.; Cooper P.;
Feron, L. J.; Bower, J. F. Branch-Selective and Enantioselec-
tive Iridium-Catalyzed Alkene Hydroarylation via Anilide-
Directed C–H Oxidative Addition. J. Am. Chem. Soc. 2018,
140, 9351–9356. (b) Loup, J.; Zell, D.; Oliveira, J. C. A.; Keil,
H.; Stalke, D.; Ackermann, L. Angew. Chem. Int. Ed. 2017,
56, 14197–14201. (c) Ebe, Y.; Onoda, M.; Nishimura, T.; Yo-
rimitsu, H. Iridium-Catalyzed Regio- and Enantioselective
Hydroarylation of Alkenyl Ethers by Olefin Isomerization.
Angew. Chem. Int. Ed. 2017, 56, 5607–5611. (d) Crisenza, G.
E. M.; Bower, J. F. Branch Selective Murai-Type Alkene
Hydroarylation Reactions. Chem. Lett. 2016, 45, 2–9; this
reference includes a discussion of other approaches to the
synthesis of 1,1-diarylalkanes. (e) Lee, P.-S.; Yoshikai, N.
Cobalt-Catalyzed Enantioselective Directed C–H Alkyla-
tion of Indole with Styrenes. Org. Lett. 2015, 17, 22-25.
For selected examples on Pd-catalyzed hydroarylation with
olefins, see: (a) Wang, H.; Bai, Z.; Jiao, T.; Deng, Z.; Tong,
H.; He, G.; Peng, Q.; Chen, G. Palladium-Catalyzed Amide-
Directed Enantioselective Hydrocarbofunctionalization of
Unactivated Alkenes Using a Chiral Monodentate Oxazo-
line Ligand. J. Am. Chem. Soc. 2018, 140, 3542–3546. (b)
Matsuura, R.; Jankins, T. C.; Hill, D. E.; Yang, K. S.; Gallego,
G. M.; Yang, S.; He, M.; Wang, F.; Marsters, R. P.; McAlpine,
1.
For biological activity of 1,1-diarylalkanes, see: (a) Soussi, M.
A.; Provot, O.; Bernadat, G.; Bignon, J.; Desravines, D.; Du-
bois, J.; Brion, J.-D.; Messaoudi, S.; Alami, M. IsoCom-
bretaQuinazolines: Potent Cytotoxic Agents with Antit-
ubulin Activity. ChemMedChem 2015, 10, 1392–1402. (b)
Messaoudi, S.; Hamze, A.; Provot, O.; Tréguier, B.; De
Losada, J. R.; Bignon, J.; Liu, J.-M.; Wdzieczak-Bakala, J.;
Thoret, S.; Dubois, J.; Brion, J.-D.; Alami, M. Discovery of
Isoerianin Analogues as Promising Anticancer Agents.
ChemMedChem 2011, 6, 488–497. (c) Cheltsov, A. V. Aoyagi,
M. Aleshin, A.; Yu, E. C.-W.; Gilliland, T.; Zhai, D.; Bobkov,
A. A.; Reed, J. C.; Liddington, R. C.; Abagyan, R. Vaccinia
Virus Virulence Factor NIL is a Novel Promising Target for
Antiviral Therapeutic Intervention. J. Med. Chem. 2010, 53,
3899–3906.
For selected reviews, see: (a) Jia, T.; Cao, P.; Liao, J. Enanti-
oselective synthesis of gem-diarylalkanes by transition
metal-catalyzed asymmetric arylations (TMCAAr). Chem.
Sci. 2018, 9, 546–559. (b) Cherney, A. H.; Kadunce, N. T.;
Reisman, S. E. Enantioselective and Enantiospecific Transi-
tion-Metal-Catalyzed Cross-Coupling Reactions of Organ-
ometallic Reagents To Construct C–C Bonds. Chem. Rev.
2015, 115, 9587–9652. (c) Tollefson, E. J.; Hanna, L. E.; Jarvo,
E. R. Acc. Chem. Res. 2015, 48, 2344–2353. (d) Swift, E. C.;
Jarvo, E. R. Asymmetric transition metal-catalyzed cross-
coupling reactions for the construction of teriary stereo-
centers. Tetrahedron 2013, 69, 5799–5817.
For selected examples, see: (a) Bess, E. N.; Sigman, M. S.
Distinctive Meta-Directing Group Effect for Iridium-
Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation.
Org. Lett. 2013, 15, 646–649. (b) Woodmansee, D. H.;
Pfaltz, A. Asymmetric hydrogenation of alkenes lacking
coordinating groups. Chem. Commun. 2011, 47, 7912–7916.
(c) Tolstoy, P.; Engman, M.; Paptchikhine, A.; Bergquist, J.;
Church, T. L.; Leung, A. W.-M.; Andersson, P. G. Iridium-
Catalyzed Asymmetric Hydrogenation Yielding Chiral Dia-
rylmethines with Weakly Coordinating or Noncoordinat-
ing Substituents. J. Am. Chem. Soc. 2009, 131, 8855–8860.
For selected examples, see: (a) Wu, C.; Yue, G.; Nielsen, C.
D.-T.; Xu, K.; Hirao, H.; Zhou, J. Asymmetric Conjugate
Addition of Organoboron Reagents to Common Enones
Using Copper Catalysts. J. Am. Chem. Soc. 2016, 138, 742–
745. (b) Takatsu, K. Shintani, R. Hayashi, T. Copper-
Catalyzed 1,4-Addition of Orgaoboronates to Alkylidene
Cyanoacetates: Mechanistic Insight and Application to
Asymmetric Catalysis. Angew. Chem. Int. Ed. 2011, 50,
5548–5552. (c) Wang, Z. Q.; Feng, C. G.; Zhang, S. S.; Xu, M.
H.; Lin, G.-Q. Rhodium-Catalyzed Asymmetric Conjugate
Addition of Organoboronic Acids to Nitroalkenes Using
Chiral Bicyclo[3.3.0] Diene Ligands. Angew. Chem. Int. Ed.
2010, 49, 5780–5783. (d) Paquin, J.-F.; Defieber, C.; Ste-
phenson, C. R. J.; Carreira, E. M. Asymmetric Synthesis of
3,3-Diarylpropanals with Chiral Diene-Rhodium Catalysts J.
Am. Chem. Soc. 2005, 127, 10850–10851.
6.
2.
3.
7.
4.
8.
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