Transition-Metal-Free Coupling Reactions

Chang-Liang Sun; Zhang-Jie Shi

doi:10.1021/cr400274j

journal article Sep 03, 2014

Transition-Metal-Free Coupling Reactions

Chang-Liang Sun Zhang-Jie Shi

Chemical Reviews Vol. 114 No. 18 pp. 9219-9280 · American Chemical Society (ACS)

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References

686

[1]

Masel R. I. (2001)

[2]

Behr A. (2002)

[3]

Elschenbroich C. (2006)

[4]

Diederich F. (1998) 10.1002/9783527612222

[5]

Bräse S. (2004)

[6]

Dyker G. (2005) 10.1002/9783527619450

[7]

Boudier A. Angew. Chem., Int. Ed. (2000) 10.1002/1521-3773(20001215)39:24<4414::aid-anie4414>3.0.co;2-c

[8]

Eisenstadt A. (2001)

[9]

Nicolaou K. C. Angew. Chem., Int. Ed. (2005) 10.1002/anie.200500368

[10]

Corbet J.-P. Chem. Rev. (2006) 10.1021/cr0505268

[11]

Magano J. Chem. Rev. (2011) 10.1021/cr100346g

[12]

Crawley M. L. (2012)

[13]

Miyaura N. Chem. Commun. (1979) 10.1039/c39790000866

[14]

Suzuki A. Acc. Chem. Res. (1982) 10.1021/ar00078a003

[15]

Suzuki A. Pure Appl. Chem. (1991) 10.1351/pac199163030419

[16]

Martin R. Acta Chem. Scand. (1993) 10.3891/acta.chem.scand.47-0221

[17]

Miyaura N. Chem. Rev. (1995) 10.1021/cr00039a007

[18]

Suzuki A. J. Organomet. Chem. (1999) 10.1016/s0022-328x(98)01055-9

[19]

Molander G. A. Acc. Chem. Res. (2007) 10.1021/ar050199q

[20]

Molander G. A. Angew. Chem., Int. Ed. (2009) 10.1002/anie.200904306

[21]

Milstein D. J. Am. Chem. Soc. (1978) 10.1021/ja00479a077

[22]

Stille J. Angew. Chem., Int. Ed. Engl. (1986) 10.1002/anie.198605081

[23]

cPereyre, M.InTin in Organic Synthesis;Butterworths:Boston, MA, 1987; pp185–207.

[24]

Mitchell T. Synthesis (1992) 10.1055/s-1992-26230

[25]

Farina V. Org. React. (1997)

[26]

Gallager W. J. Am. Chem. Soc. (2001) 10.1021/ja0035295

[27]

aTamao, K.InComprehensive Organic Synthesis;Trost, B., Ed.Permagon:Oxford, 1991; Vol.3, pp435–480.

[28]

Terao J. Acc. Chem. Res. (2008) 10.1021/ar800138a

[29]

Knappke C. E. I. Chem. Soc. Rev. (2011) 10.1039/c1cs15137a

[30]

Beak P. Acc. Chem. Soc. (1996) 10.1021/ar950142b

[31]

Hoppe D. Angew. Chem., Int. Ed. (1997) 10.1002/anie.199722821

[32]

Clayden J. (2002)

[33]

Hogson D. M. (2003) 10.1007/3-540-36117-0

[34]

Negishi E. J. Org. Chem. (1977) 10.1021/jo00430a041

[35]

Negishi E. Acc. Chem. Res. (1982) 10.1021/ar00083a001

[36]

Knochel P. Chem. Rev. (1993) 10.1021/cr00022a008

[37]

Knochel P. Chem. Ber./Recl. (1997) 10.1002/cber.19971300802

[38]

Erdik E. Tetrahedron (1998)

[39]

Knochel P. Angew. Chem., Int. Ed. (2003) 10.1002/anie.200300579

[40]

Phapale V. B. Chem. Soc. Rev. (2009) 10.1039/b805648j

[41]

Hatanaka Y. Synlett (1991) 10.1055/s-1991-20899

[42]

Hiyama T. Pure Appl. Chem. (1994) 10.1351/pac199466071471

[43]

cHiyama, T.InMetal-Catalyzed Cross-Coupling Reactions;Diederich, F.; Stang, J., Eds.Wiley-VCH:Weinheim, 1998; Chapter 10, pp421–454.

[44]

Demnark S. E. Acc. Chem. Res. (2002) 10.1021/ar020001r

[45]

Denmark S. E. Acc. Chem. Res. (2008) 10.1021/ar800037p

[46]

Sore H. F. Chem. Soc. Rev. (2012) 10.1039/c1cs15181a

[47]

Heck R. F. J. Org. Chem. (1972) 10.1021/jo00979a024

[48]

Heck R. F. Org. React. (1982)

[49]

de Meijere A. Angew. Chem., Int. Ed. (1994) 10.1002/anie.199423791

[50]

Cabri W. Acc. Chem. Res. (1995) 10.1021/ar00049a001

Showing 50 of 686 references

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Details

Published: Sep 03, 2014
Vol/Issue: 114(18)
Pages: 9219-9280

Authors

C

Chang-Liang Sun

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, 202 Chengfu Road, 098#, Beijing 100871, China; State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 200060, China

Z

Zhang-Jie Shi

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, 202 Chengfu Road, 098#, Beijing 100871, China; State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 200060, China

Funding

National Natural Science Foundation of China Award: 21332001

Ministry of Science and Technology Award: 2009CB825300

Cite This Article

Chang-Liang Sun, Zhang-Jie Shi (2014). Transition-Metal-Free Coupling Reactions. Chemical Reviews, 114(18), 9219-9280. https://doi.org/10.1021/cr400274j

Transition-Metal-Free Coupling Reactions

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