Developing Pd(II) Catalyzed Double sp3 C–H Alkoxylation for Synthesis of Symmetric and Unsymmetric Acetals

Yu Zong; Yu Rao

doi:10.1021/ol502377x

journal article Sep 29, 2014

Developing Pd(II) Catalyzed Double sp3 C–H Alkoxylation for Synthesis of Symmetric and Unsymmetric Acetals

Yu Zong

Yu Rao

Organic Letters Vol. 16 No. 20 pp. 5278-5281 · American Chemical Society (ACS)

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References

53

[1]

aGreen,T. W.; Wuts, P. G. M.Protective Groups in Organic Synthesis;Wiley-Interscience:New York, 1999; p297. 10.1002/0471220574

[2]

Clode D. M. Chem. Rev. (1979) 10.1021/cr60322a002

[3]

Barbaro P. J. Mol. Catal. (1999) 10.1016/s1381-1169(99)00016-3

[4]

Procuranti B. Org. Lett. (2008) 10.1021/ol802008m

[5]

Clerici A. Tetrahedron (1998) 10.1016/s0040-4020(98)00982-x

[6]

Cataldo M. J. Mol. Catal. (1999) 10.1016/s1381-1169(98)00299-4

[7]

Ott J. New J. Chem. (1990)

[8]

Luche J. L. J. Chem. Soc., Chem. Commun. (1978) 10.1039/c39780000976

[9]

Kim J. H. Angew. Chem., Int. Ed. (2013) 10.1002/anie.201300120

[10]

Eshghi H. Catal. Commun. (2008) 10.1016/j.catcom.2008.06.015

[11]

Ji S. J. J. Mol. Catal. (2003) 10.1016/s1381-1169(03)00210-3

[12]

Yamanaka D. Tetrahedron Lett. (2008) 10.1016/j.tetlet.2007.11.018

[13]

Kumar R. Tetrahedron Lett. (2005) 10.1016/j.tetlet.2005.09.168

[14]

Yamanaka D. Tetrahedron Lett. (2008) 10.1016/j.tetlet.2007.11.018

[15]

Chen C. J. Am. Chem. Soc. (2010) 10.1021/ja104523y

[16]

Ruan J. Acc. Chem. Res. (2011) 10.1021/ar200053d

[17]

Sherry B. D. J. Am. Chem. Soc. (2006) 10.1021/ja061344d

[18]

Ruan J. Acc. Chem. Res. (2011) 10.1021/ar200053d

[19]

Krompieca S. Coord. Chem. Rev. (2012) 10.1016/j.ccr.2012.05.006

[20]

Gopinath R. J. Org. Chem. (2002) 10.1021/jo025701o

[21]

Alberico D. Chem. Rev. (2007) 10.1021/cr0509760

[22]

Colby D. A. Chem. Rev. (2010) 10.1021/cr900005n

[23]

Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

Thomas W. Lyons, Melanie S. Sanford

Chemical Reviews 2010 10.1021/cr900184e

[24]

Xu L. M. Chem. Soc. Rev. (2010) 10.1039/b809912j

[25]

Wencel-Delord J. Chem. Soc. Rev. (2011) 10.1039/c1cs15083a

[26]

Chen X. Angew. Chem. (2009) 10.1002/ange.200806273

[27]

Angew. Chem., Int. Ed. 2009, 48, 5094. 10.1002/anie.200990240

[28]

Controlling Site Selectivity in Palladium-Catalyzed C–H Bond Functionalization

Sharon R. Neufeldt, Melanie S. Sanford

Accounts of Chemical Research 2012 10.1021/ar300014f

[29]

Johnson J. A. J. Am. Chem. Soc. (2000) 10.1021/ja0003223

[30]

Hinman A. J. Am. Chem. Soc. (2003) 10.1021/ja0368305

[31]

Davies H. M. L. J. Am. Chem. Soc. (2006) 10.1021/ja056877l

[32]

Stang E. M. Nat. Chem. (2009) 10.1038/nchem.351

[33]

Chaumontet M. Angew. Chem. (2009) 10.1002/ange.200804444

[34]

Angew. Chem., Int. Ed. 2009, 48, 179. 10.1002/anie.200990240

[35]

Feng Y. Angew. Chem. (2010) 10.1002/ange.200905134

[36]

Angew. Chem., Int. Ed. 2010, 49, 958. 10.1002/anie.201090153

[37]

Gutekunst W. R. J. Am. Chem. Soc. (2011) 10.1021/ja209205x

[38]

Wasa M. J. Am. Chem. Soc. (2009) 10.1021/ja903573p

[39]

Wasa M. J. Am. Chem. Soc. (2010) 10.1021/ja1010866

[40]

Wasa M. J. Am. Chem. Soc. (2011) 10.1021/ja207607s

[41]

Gutekunst W. R. Angew. Chem. (2012) 10.1002/ange.201203897

[42]

Angew. Chem., Int. Ed. 2012, 51, 7507. 10.1002/anie.201290081

[43]

Shan G. Angew. Chem., Int. Ed. (2013) 10.1002/anie.201307090

[44]

Chen F. J. Chem. Sci. (2013) 10.1039/c3sc51993g

[45]

Highly Regioselective Arylation of sp3 C−H Bonds Catalyzed by Palladium Acetate

Vladimir G. Zaitsev, Dmitry Shabashov, Olafs Daugulis

Journal of the American Chemical Society 2005 10.1021/ja054549f

[46]

Shabashov D. J. Am. Chem. Soc. (2010) 10.1021/ja910900p

[47]

Zhang S. Y. J. Am. Chem. Soc. (2013) 10.1021/ja406484v

[48]

Canty A. J. Acc. Chem. Res. (1992) 10.1021/ar00014a005

[49]

Angew. Chem., Int. Ed. (2009) 10.1002/anie.200903671

[50]

Sehnal P. Chem. Rev. (2010) 10.1021/cr9003242

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Details

Published: Sep 29, 2014
Vol/Issue: 16(20)
Pages: 5278-5281

Authors

Y

Yu Zong

MOE Key Laboratory of Protein Sciences, Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing 100084, China

Y

Yu Rao

MOE Key Laboratory of Protein Sciences, Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing 100084, China

Funding

National Natural Science Foundation of China Award: 21302106

Tsinghua University

Ministry of Science and Technology of the People's Republic of China Award: 2011CB965300

Cite This Article

Yu Zong, Yu Rao (2014). Developing Pd(II) Catalyzed Double sp3 C–H Alkoxylation for Synthesis of Symmetric and Unsymmetric Acetals. Organic Letters, 16(20), 5278-5281. https://doi.org/10.1021/ol502377x

Developing Pd(II) Catalyzed Double sp3 C–H Alkoxylation for Synthesis of Symmetric and Unsymmetric Acetals

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