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Progress in Chemistry 2010, Vol. 22 Issue (07): 1403-1413 Previous Articles   Next Articles

• Invited Article •

Decarboxylative C-C Bond Formations

Feng Chao1    Liu Saiwen1    Peng Shengming1    Yi Bing 2    Deng Guojun1**   

  1. (1. Key Laboratory for Environmental Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China；2. College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104, China)
  • Received: Online: Published:
  • Contact: Deng Guojun E-mail:gjdeng@xtu.edu.cn
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Carboxylic acid or carboxylate groups are among the most common functionalities in organic molecules. Activated derivatives of carboxylic acids have long served as versatile connection points in derivatizations and in the construction of carbon frameworks. Carboxylic acids are cheap and high availability. Decarboxylative reaction provides a new approach for organic synthesis. The carboxylic acid functionality ensures the regioselectivity of the reaction and only carbon dioxide is produced as waste. Thus decarboxylative reactions meet the requirement of green chemistry and its application in organic synthesis is very promising. Many reviews have been published on decarboxylative reactions. This review mainly focused on the progress of decarboxylative C-C bond formation during the past several years.

Contents 
1 Introduction 
2 Decarboxylative cross-coupling reaction 
3 Decarboxylative Heck-type reaction 
4 Decarboxylative allylation 
5 Decarboxylative aldol and Mannich reaction 
6 Decarboxylative Claisen rearrangement reaction 
7 Decarboxylative addition 
8 Conclusions and outlook

Key words: carboxylic acids, decarboxylation, C-C bond formation, green chemistry

CLC Number: 

［1 ］ Diederich F， Stang P T. Metal-Catalyzed Cross-Coupling
Reactions. Weiheim: Wiley-VCH，1998
［2 ］ Chatani N. Cross-Coupling Reactions. New York: Springer，
2002
［3 ］ Alberico D，Scott M E，Lautens M. Chem. Rev. ，2007，107:
174—238
［4 ］ Yin L X，Liebscher J. Chem. Rev. ，2007，107: 133—173
［5 ］ Miyaura N，Suzuki A. Chem. Rev. ，1995，95: 2457—2483
［6 ］ Anastas P T， Warner J C. Green Chemistry: Theory and
Practice. New York: Oxford University Press，1998
［7 ］ Li C J. Acc. Chem. Res. ，2009，42: 335—344
［8 ］ Ritleng V， Sirlin C， Pfeffer M. Chem. Rev. ，2002，102:
1731—1770
［9 ］ Ackermann L. Chelation-Assisted Arylation via C—H Bond
Cleavage. Top. Organomet. Chem. ，2007，24: 35—60
［10］ Michael B S，March J. March’s Advanced Organic Chemistry.
New York: Wiley，2007
［11］ Vollhardt K P C，Schore N E. Organische Chemie. 3rd ed.
Weinheim: Wiley，2000. 1081 —1087
［12］ March J. Advanced Organic Chemistry. New York: Wiley，
1992. 1183—1184
［13］ Goossen L J，Rodríguez N，Goossen K. Angew. Chem. Int.
Ed. ，2008，47: 3100—3120
［14］ Goossen L J，Ghosh K. Angew. Chem. Int. Ed. ，2001，40:
3458—3460
［15］ Goossen L J，Ghosh K. Chem. Commun. ，2002，836—837
［16］ Tsuji J，Ohno K. Synthesis，1969，157—169
［17］ Nilsson M. Acta. Chem. Scand. ，1966，20: 423—426
［18］ Goossen L J，Deng G J，Levy L M. Science，2006，313: 662—
664
［19］ Goossen L J，Rodriguez N，Deng G J，et al. J. Am. Chem.
Soc. ，2007，129: 4824—4833
［20］ Baudoin O. Angew. Chem. Int. Ed. ，2007，46: 1373—1375
［21］ Bonesi S，Fagnoni M，Albini A. Angew. Chem. Int. Ed. ，
2008，47: 10022—10025
［22］ Goossen L J，Zimmermann B，Knauber T. Angew. Chem. Int.
Ed. ，2008，47: 7103—7106
［23］ Goossen L J，Rodriguez N，Melzer B，Linger C. J. Am. Chem.
Soc. ，2008，130: 15240—15249
［24］ Goossen L J，Rudolphi F，Oppel C，Rodriguez N. Angew.
Chem. Int. Ed. ，2008，47: 3043—3045
［25］ Shang R，Fu Y，Liu L，et al. J. Am. Chem. Soc. ，2009，131:
5738—5739
［26］ Yu W Y，Chan A S C，Zhou Z Y，et al. Org. Lett. ，2009，11:
3174—3177
［27］ Forgione P，Bilodeau F，Brochu M C，et al. J. Am. Chem.
Soc. ，2006，128: 11350—11351
［28］ Becht J M，Catala C，Drian C L，Wagner A. Org. Lett. ，2007，
9 : 1781—1783
［29］ Miyasaka M，Miura M，Satoh T，et al. Chem. Eur. J. ，2009，
15: 3674—3677
［30］ Voutchkova A， Coplin A， Leadbeater N E， Crabtree R H.
Chem. Commun. ，2008，6312—6314
［31］ Wang C Y，Piel I，Glorius F. J. Am. Chem. Soc. ，2009，131:
4194—4195
［32］ Shang R，Fu Y，Liu L，et al. Angew. Chem. Int. Ed. ，2009，
48: 9350—9354
［33］ Bi H P，Zhao L，Liang Y M，Li C J. Angew. Chem. Int. Ed. ，
2009，48: 792—795
［34］ Bi H P，Chen W W，Liang Y M，Li C J. Org. Lett. ，2009，
15: 3246—3249
［35］ Mizoroki T，Mori K，Ozaki A. Bull. Chem. Soc. Jpn. ，1971，
44: 581—584
［36］ Heck R F，Nolley J P. J. Org. Chem. ，1972，14: 2320—2322
［37］ Heck R F. Org. React. ，1982，27: 345—390
［38］ Meijere A，Meyer F E. Angew. Chem. Int. Ed. ，1994，32:
2379—2411
［39］ Cabri W，Candiani I. Acc. Chem. Res. ，1995，28: 2—7
［40］ Beletskaya I P，Cheprakov A V. Chem. Rev. ，2000，100:
3009—3066
［41］ Whitcombe N T，Hii K K，Gibson S E. Tetrahedron，2001，57:
7449—7476
［42］ Myers A G，Tanaka D，Mannion M R. J. Am. Chem. Soc. ，
2002，124: 11250—11251
［43］ Tanaka D，Myers A G. Org. Lett. ，2004，6: 433—436
［44］ Tanaka D，Romeril S P，Myers A G. J. Am. Chem. Soc. ，
2005，127: 10323—10333
［45］ Huang X C，Wang F，Liang Y，Li J H. Org. Lett. ，2009，11:
1139—1142
［46］ Rayabarapu D K，Tunge J A. J. Am. Chem. Soc. ，2005，127:
13510—13511
［47］ Bloch R. Chem Rev. ，1998，98: 1407—1438
［48］ Burger E C，Tunge J A. J. Am. Chem. Soc. ，2006，128:
10002—10003
［49］ Waetzig S R，Tunge J A. J. Am. Chem. Soc. ，2007，129:
4138—4139
［50］ Waetzig S R，Tunge J A. J. Am. Chem. Soc. ，2007，129:
14860—14861
［51］ Mohr J T，Behenna D C，Harned A M，Stoltz B M. Angew.
Chem. Int. Ed. ，2005，44: 6924—6927
［52］ Mohr J T，Nishimata T，Behenna D C，Stoltz B M. J. Am.
Chem. Soc. ，2006，128: 11348—11349
［53］ Trost B M，Xu J Y，Schmitdt T. J. Am. Chem. Soc. ，2009，
131: 18343—18357
［54］ Comprehensive Organic Synthesis ( Eds. Trost B M，Fleming I) .
Oxford: Pergamon Press，1991
［55］ Lalic G，Aloise A D，Shair M D. J. Am. Chem. Soc. ，2003，
125: 2852—2853
［56］ Lou S，Westbrook J A，Schaus S E. J. Am. Chem. Soc. ，
2004，126: 11440—11441
［57］ Blaquiere N，Shore D G，Rousseaux S，Fagnou K. J. Org.
Chem. ，2009，74: 6190—6198
［58］ Yin L，Kanai M，Shibasaki M. J. Am. Chem. Soc. ，2009，
131: 9610—9611
［59］ Castro A M M. Chem. Rev. ，2004，104: 2939—3002
［60］ Craig D，Grellepois F. Org. Lett. ，2005，5: 463—465
［61］ Bourgeois D，Craig D，King N P，Mountford D M. Angew.
Chem. Int. Ed. ，2005，44: 618—621
［62］ Yoshida K， Hayashi T. Modern Rhodium-Catalyzed Organic
Reactions. Weinheim: Wiley-VCH，2005
［63］ Hayashi T，Yamasaki K. Chem. Rev. ，2003，103: 2829—
2844
［64］ Sun Z M，Zhao P J. Angew. Chem. Int. Ed. ，2009，47:
6726—6730
［65］ Kajita Y，Kurahashi T，Matsubara S. J. Am. Chem. Soc. ，
2008，130: 6058—6059
［66］ Yoshino Y，Kurahashi T，Matsubara S. J. Am. Chem. Soc. ，
2009，131: 7494—7495
［67］ Duan Z Y，Ranjit S，Zhang P F，Liu X G. Chem. Eur. J. ，
2009，15: 3666—3669
［68］ Goossen L J，Dhring A. Adv. Synth. Catal. ，2003，345:
943—947
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Abstract

Decarboxylative C-C Bond Formations