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DOI: 10.1055/s-0031-1290101
Recent Advances in Transition-Metal-Catalyzed Esterification
Publication History
Publication Date:
09 December 2011 (online)
Abstract
In this account, we summarized our recent progress in transition-metal-catalyzed esterification via different pathways, including lactonization, Chan-Lam reaction, oxidative esterification and C-H functionalization.
1 Introduction
2 Esterification of Aldehyde with Aryl Boron
2.1 Aromatic Esterification Reaction between Aldehydes and Arylboronic Acids
2.2 Cascade Aryl Addition-Lactonization of Phthalaldehyde with Aryl Boron
2.3 Cascade Aryl Addition-Lactonization of Phthalaldehydonitrile with Arylboronic Acids
3 Esterification of Carboxylic Acid via Chan-Lam Reaction
4 Bis-esterification of Cyclic Anhydrides with Alkoxysilanes
5 Oxidative Esterification of Aldehydes or Benzylic Alcohols with Phenols
6 Ester Formation via C-H Functionalization
6.1 Benzoxylation of C-H Bonds with Carboxylic Acids
6.2 Benzoxylation of 2-Arylpyridine sp² C-H Bonds with Anhydrides
6.3 Benzoxylation of 2-Arylpyridine sp² C-H Bonds with Acyl Chlorides
7 Conclusion
Key words
esterification - transition metals - catalysis - esters - C-H functionalization
-
1a
Larock RC. Comprehensive Organic Transformations VCH; New York: 1989. p.966 ; and references therein -
1b
Otera J. Esterification: Methods Reactions and Applications Wiley; New York: 2003. -
2a
Moretto A.Nicolli A.Lotti M. Toxicol. Appl. Pharmacol. 2007, 219: 196 -
2b
Beginn U.Zipp G.Moller M. Chem.-Eur. J. 2000, 6: 2016 -
2c
Barratt MD.Basketter DA.Roberts DW. Toxicol. Vitro 1994, 8: 823 -
2d
Child JJ.Oka T.Simpson FJ.Krishnamurty HG. Can. J. Microbiol. 1971, 17: 1455 -
2e
Dong Y.Shi Q.Pai H.-C.Peng C.-Y.Pan S.-L.Teng C.-M.Nakagawa-Goto K.Yu D.Liu Y.-N.Wu P.-C.Bastow KF.Morris-Natschke SL.Brossi A.Lang J.-Y.Hsu JL.Hung M.-C.Lee EY.-HP.Lee K.-H. J. Med. Chem. 2010, 53: 2299 -
2f
Nemoto T.Yamamoto N.Watanabe A.Fujii H.Hasebe K.Nakajima M.Mochizuki H.Nagase H. Bioorg. Med. Chem. 2011, 19: 1205 -
2g
Petersen TB.Khan R.Olofsson B. Org. Lett. 2011, 13: 3462 -
2h
Thasana N.Worayuthakarn R.Kradanrat P.Hohn E.Young L.Ruchirawat S. J. Org. Chem. 2007, 72: 9379 -
2i
Zakhari JS.Kinoyama I.Struss AK.Pullanikat P.Lowery CA.Lardy M.Janda KD. J. Am. Chem. Soc. 2011, 133: 3840 -
3a
Ishihara K. Tetrahedron 2009, 65: 1085 -
3b
Iranpoor N.Firouzabadi H.Khalili D. Org. Biomol. Chem. 2010, 8: 4436 -
3c
Lee CK.Yu JS.Lee H.-J. J. Heterocycl. Chem. 2002, 39: 1207 -
3d
Eshghi H.Rafei M.Karimi MH. Synth. Commun. 2001, 31: 771 -
3e
Ueda M.Mori H. Bull. Chem. Soc. Jpn. 1992, 65: 1636 -
3f
Ueda M.Oikawa H. J. Org. Chem. 1985, 50: 760 -
3g
Keshavamurthy KS.Vankar YD.Dhar DN. Synthesis 1982, 506 -
3h
Nowrouzi N.Mehranpour AM.Rad JA. Tetrahedron 2010, 66: 9596 -
4a
Otera J. Acc. Chem. Res. 2004, 37: 288 -
4b
Grasa GA.Singh R.Nolan SP. Synthesis 2004, 971 -
4c
Shinada T.Hamada M.Miyoshi K.Higashino M.Umezawa T.Ohfune Y. Synlett 2010, 2141 -
4d
Hatano M.Furuya Y.Shimmura T.Moriyama K.Kamiya S.Maki T.Ishihara K. Org. Lett. 2011, 13: 426 -
4e
Bose DS.Satyender A.Rudra Das AP.Mereyala HB. Synthesis 2006, 2392 -
4f
Iwasaki T.Maegawa Y.Hayashi Y.Ohshima T.Mashima K. J. Org. Chem. 2008, 73: 5147 -
4g
Remme N.Koschek K.Schneider C. Synlett 2007, 491 -
5a
Fischer E. Ber. Dtsch. Chem. Ges. 1895, 28: 3254 -
5b
Butts J. J. Am. Chem. Soc. 1931, 53: 3560 -
6a
Brink G.-J.Arends IWCE.Sheldon RA. Chem. Rev. 2004, 104: 4105 -
6b
Kotsuki H.Arimura K.Araki T.Shinohara T. Synlett 1999, 462 -
6c
Yadav JS.Reddy BVS.Basak AK.Narsaiah AV. Chem. Lett. 2004, 33: 248 -
6d
Olah GA.Wang Q.Trivedi NJ.Prakash GKS. Synthesis 1991, 739 -
6e
Yoshida Y.Murakami K.Yorimitsu H.Oshima K. J. Am. Chem. Soc. 2010, 132: 9236 -
7a
Reynolds NT.Read de Alaniz J.Rovis T. J. Am. Chem. Soc. 2004, 126: 9518 -
7b
Kiyooka S.-I.Wada Y.Ueno M.Yokoyama T.Yokoyama R. Tetrahedron 2007, 63: 12695 -
7c
Gopinath R.Patel BK. Org. Lett. 2000, 2: 577 -
7d
Barkakaty B.Talukdar B.Patel BK. J. Org. Chem. 2003, 68: 2944 -
7e
Rose CA.Zeitler K. Org. Lett. 2010, 12: 4552 -
7f
Travis BR.Sivakumar M.Hollist GO.Borhan B. Org. Lett. 2003, 5: 1031 -
7g
Kiran YB.Ikeda R.Sakai N.Konakahara T. Synthesis 2010, 276 -
7h
Gopinath R.Paital AR.Patel BK. Tetrahedron Lett. 2002, 43: 5123 -
7i
Jiang H.Gschwend B.Albrecht .Jørgensen KA. Org. Lett. 2010, 12: 5052 -
7j
Gligorich KM.Sigman MS. Chem. Commun. 2009, 3854 -
7k
Reynolds NT.Rovis T. J. Am. Chem. Soc. 2005, 127: 16406 -
7l
Maki BE.Chan A.Phillips EM.Scheidt KA. Org. Lett. 2007, 9: 371 -
7m
Sarkar SD.Grimme S.Studer A. J. Am. Chem. Soc. 2010, 132: 1190 -
7n
Maji B.Vedachalan S.Ge X.Cai S.Liu X.-W. J. Org. Chem. 2011, 76: 3016 -
7o
De Sarkar S.Biswas A.Song CH.Studer A. Synthesis 2011, 1974 -
8a
Yang C.-G.He C. J. Am. Chem. Soc. 2005, 127: 6966 -
8b
Ekoue-Kovi K.Wolf C. Chem.-Eur. J. 2008, 14: 6302 -
8c
Ishihara K.Ohara S.Yamamoto H. Science 2000, 290: 1140 -
8d
Kaizuka K.Miyamura H.Kobayashi S. J. Am. Chem. Soc. 2010, 132: 15096 -
8e
Nakatani Y.Koizumi Y.Yamasaki R.Saito S. Org. Lett. 2008, 10: 2067 -
8f
Dai J.-J.Liu J.-H.Luo D.-F.Liu L. Chem. Commun. 2011, 47: 677 -
8g
Rosa JN.Reddy RS.Candeias NR.Cal PMSD.Gois PMP. Org. Lett. 2010, 12: 2686 -
8h
Guo C.Yue X.Qing F.-L. Synthesis 2010, 1837 -
8i
Kuriyama M.Ishiyama N.Shimazawa R.Shirai R.Onomura O. J. Org. Chem. 2009, 74: 9210 -
8j
Gnanaprakasam B.Ben-David Y.Milstein D. Adv. Synth. Catal. 2010, 352: 3169 -
8k
Xing C.-H.Liao Y.-X.He P.Hu Q.-S. Chem. Commun. 2010, 46: 3010 -
8l
Mihara M.Nakai T.Iwai T.Ito T.Ohno T.Mizuno T. Synlett 2010, 253 -
8m
Hoshimoto Y.Ohashi M.Ogoshi S. J. Am. Chem. Soc. 2011, 133: 4668 -
8n
Wu X.-F.Neumann H.Beller M. ChemCatChem 2010, 2: 509 -
8o
Bottalico D.Fiandanese V.Marchese G.Punzi A. Synlett 2007, 974 -
8p
Tang S.Peng P.Wang Z.-Q.Tang B.-X.Deng C.-L.Li J.-H.Zhong P.Wang N.-X. Org. Lett. 2008, 10: 1875 -
8q
Kawatsura M.Namioka J.Kajita K.Yamamoto M.Tsuji H.Itoh T. Org. Lett. 2011, 13: 3285 - 9
Qin C.Wu H.Cheng J.Chen X.Liu M.Zhang W.Su W.Ding J. J. Org. Chem. 2007, 72: 4102 - 10
Qin C.Chen J.Wu H.Cheng J.Zhang Q.Zuo B.Su W.Ding J. Tetrahedron Lett. 2008, 49: 1884 - 11
Qin C.Wu H.Chen J.Liu M.Cheng J.Su W.Ding J. Org. Lett. 2008, 10: 1537 -
12a
Sakai M.Ueda M.Miyaura N. Angew. Chem. Int. Ed. 1998, 37: 3279 -
12b
Duan H.-F.Xie J.-H.Shi W.-J.Zhang Q.Zhou Q.-L. Org. Lett. 2006, 8: 1479 -
12c
Fürstner A.Krause H. Adv. Synth. Catal. 2001, 343: 343 -
12d
Morikawa S.Michigami K.Amii H. Org. Lett. 2010, 12: 2520 -
12e
Gois PMP.Trindade AF.Veiros LF.Andre V.Duarte MT.Afonso CAM.Caddick S.Cloke FGN. Angew. Chem. Int. Ed. 2007, 46: 5750 -
12f
Chen W.Baghbanzadeh M.Kappe CO. Tetrahedron Lett. 2011, 52: 1677 -
12g
Yamamoto T.Ohta T.Ito Y. Org. Lett. 2005, 7: 4153 -
12h
Zheng H.Ding J.Chen J.Liu M.Gao W.Wu H. Synlett 2011, 1626 -
12i
Liao Y.-X.Xing C.-H.He P.Hu Q.-S. Org. Lett. 2008, 10: 2509 -
12j
Kuriyama M.Ishiyama N.Shimazawa R.Onomura O. Tetrahedron 2010, 66: 6814 -
12k
Zou T.Pi S.-S.Li J.-H. Org. Lett. 2009, 11: 453 -
12l
Trindade AF.Andre V.Duarte MT.Veiros LF.Gois PMP.Afonso CAM. Tetrahedron 2010, 66: 8494 -
12m
Karthikeyan J.Jeganmohan M.Cheng C.-H. Chem.-Eur. J. 2010, 16: 8989 -
12n
Liu G.Lu X. J. Am. Chem. Soc. 2006, 128: 16504 -
12o
Yamamoto K.Tsurumi K.Sakurai F.Kondo K.Aoyama T. Synthesis 2008, 3585 -
13a
Beck JJ.Chou S.-C. J. Nat. Prod. 2007, 70: 891 -
13b
Tianpanich K.Prachya S.Wiyakrutta S.Mahidol C.Ruchirawat S.Kittakoop P. J. Nat. Prod. 2011, 74: 79 -
13c
Lee TF.Lin YL.Huang YT. Planta Med. 2007, 73: 527 -
13d
Puder C.Zeeck A.Beil W. J. Antibiot. 2000, 53: 329 -
13e
Singh M.Argade NP. J. Org. Chem. 2010, 75: 3121 -
13f
Knepper K.Ziegert RE.Bräse ST. Tetrahedron 2004, 60: 8591 -
13g
Choi PJ.Sperry J.Brimble MA. J. Org. Chem. 2010, 75: 7388 -
13h
Xiong MJ.Li ZH. Curr. Org. Chem. 2007, 11: 833 -
13i
Shode FO.Mahomed AS.Rogers CB. Phytochemistry 2002, 61: 955 -
13j
Zhang H.Zhang S.Liu L.Luo G.Duan W.Wang W. J. Org. Chem. 2010, 75: 368 -
13k
Witulski B.Zimmermann A.Gowans ND. Chem. Commun. 2002, 2984 - 14
Ye Z.Lv G.Wang W.Zhang M.Cheng J. Angew. Chem. Int. Ed. 2010, 49: 3671 - 15
Mikami K.Ohmura H. Org. Lett. 2002, 4: 3355 - 16
Ye Z.Qian P.Lv G.Luo F.Cheng J. J. Org. Chem. 2010, 75: 6043 - 17
Karthikeyan J.Parthasarathy K.Cheng C.-H. Chem. Commun. 2011, 47: 10461 -
18a
Suzuki A. Acc. Chem. Res. 1982, 15: 178 -
18b
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
18c
Suzuki A.
J. Organomet. Chem. 1998, 576: 147 - 19
Onak T. Organoborane Chemistry Academic Press; New York: 1975. - Reviews:
-
20a
Molander GA.Figueroa R. Aldrichimica Acta 2005, 38: 49 -
20b
Molander GA.Ellis N. Acc. Chem. Res. 2007, 40: 275 -
20c
Stefani HA.Cella R.Adriano S. Tetrahedron 2007, 63: 3623 -
20d
Darses S.Genet J.-P. Chem. Rev. 2008, 108: 288 -
21a
Molander GA.Canturk B. Angew. Chem. Int. Ed. 2009, 48: 9240 -
21b
Molander GA.Canturk B.Kennedy LE. J. Org. Chem. 2009, 74: 973 -
21c
Knapp DM.Gillis EP.Burke MD. J. Am. Chem. Soc. 2009, 131: 6961 - Reviews:
-
22a
Fagnou K.Lautens M. Chem. Rev. 2003, 103: 169 -
22b
Miyaura N. Synlett 2009, 2039 -
22c
Díez-González S.Marion N.Nolan SP. Chem. Rev. 2009, 109: 3612 -
23a
Batey RA.Thadani AN.Smil DV. Org. Lett. 1999, 1: 1683 -
23b
Pucheault M.Darses S.Genet J.-P. Chem. Commun. 2005, 4714 -
23c
Kuriyama M.Shimazawa R.Enomoto T.Shirai R. J. Org. Chem. 2008, 73: 6939 -
23d
Sakurai F.Kondo K.Aoyama T. Chem. Pharm. Bull. 2009, 57: 511 - 24
Luo F.Pan S.Pan C.Qian P.Cheng J. Adv. Synth. Catal. 2011, 353: 320 -
25a
Zhou C.Larock RC. J. Am. Chem. Soc. 2004, 126: 2302 -
25b
Zhou C.Larock RC. J. Org. Chem. 2006, 71: 3551 -
25c
Tian Q.Pletnev AA.Larock RC. J. Org. Chem. 2003, 68: 339 -
25d
Pletnev AA.Tian Q.Larock RC. J. Org. Chem. 2002, 67: 9276 -
25e
Pletnev AA.Larock RC. Tetrahedron Lett. 2002, 43: 2133 -
25f
Pletnev AA.Tian Q.Larock RC. J. Org. Chem. 2002, 67: 9428 -
26a
Zhao B.Lu X. Org. Lett. 2006, 8: 5987 -
26b
Zhao L.Lu X. Angew. Chem. Int. Ed. 2002, 41: 4343 -
26c
Zhao B.Lu X. Tetrahedron Lett. 2006, 47: 6765 -
27a
Miura T.Nakazawa H.Murakami M. Chem. Commun. 2005, 2855 -
27b
Miura T.Murakami M. Org. Lett. 2005, 7: 3339 -
27c
Shimizu H.Murakami M. Chem. Commun. 2007, 2855 -
27d
Miura T.Harumashi T.Murakami M. Org. Lett. 2007, 9: 741 - 28
Lv G.Huang G.Zhang G.Pan C.Chen F.Cheng J. Tetrahedron 2011, 67: 4879 - 29
Qiao JX.Lam PYS. Synthesis 2011, 829 -
30a
Quach TD.Batey RA. Org. Lett. 2003, 5: 1381 -
30b
Petrassi HM.Sharpless KB.Kelly JW. Org. Lett. 2001, 3: 139 -
30c
Decicco CP.Song Y.Evans DA. Org. Lett. 2001, 3: 1029 -
30d
Evans DA.Katz JL.West TR. Tetrahedron Lett. 1998, 39: 2937 -
30e
Jung ME.Lazarova TI. J. Org. Chem. 1999, 64: 2976 -
30f
Blouin M.Frenette R. J. Org. Chem. 2001, 66: 9043 - 31
Luo F.Pan C.Cheng J. Curr. Org. Chem. 2011, 15: 2816 - 32
Luo F.Pan C.Qian P.Cheng J. Synthesis 2010, 2005 - 33
Zhang L.Zhang G.Zhang M.Cheng J. J. Org. Chem. 2010, 75: 7472 - 34
Lerebours R.Wolf C. J. Am. Chem. Soc. 2006, 128: 13052 - 35
Luo F.Pan C.Qian P.Cheng J. J. Org. Chem. 2010, 75: 5379 - 36
Zhang M.Zhang S.Zhang G.Chen F.Cheng J. Tetrahedron Lett. 2011, 52: 2480 -
37a
Dobereiner GE.Crabtree RH. Chem. Rev. 2010, 110: 681 -
37b
Obora Y.Ishii Y. Synlett 2011, 30 -
37c
Zhang J.Leitus G.Ben-David Y.Milstein D. J. Am. Chem. Soc. 2005, 127: 10840 -
37d
Gunanathan C.Shimon LJW.Milstein D. J. Am. Chem. Soc. 2009, 131: 3146 -
37e
Owston NA.Parker AJ.Williams JMJ. Chem. Commun. 2008, 624 -
37f
Miyamura H.Yasukawa T.Kobayashi S. Green Chem. 2010, 12: 776 -
37g
Mori N.Togo H. Tetrahedron 2005, 61: 5915 -
37h
Coleman MG.Brown AN.Bolton BA.Guana H. Adv. Synth. Catal. 2010, 352: 967 -
37i
Maki BE.Chan A.Phillips EM.Scheidt KA. Tetrahedron 2009, 65: 3102 -
37j
Owston NA.Nixon TD.Parker AJ.Whittlesey MK.Williams JMJ. Synthesis 2009, 1578 -
37k
Yamamoto N.Obora Y.Ishii Y. J. Org. Chem. 2011, 76: 2937 -
37l
Zweifel T.Naubron J.-V.Büttner T.Ott T.Grützmacher H. Angew. Chem. Int. Ed. 2008, 47: 3245 -
37m
Arita S.Koike T.Kayaki Y.Ikariya T. Chem. Asian J. 2008, 3: 1479 - 38
Luo F.Pan C.Cheng J.Chen F. Tetrahedron 2011, 67: 5878 -
39a
Liu C.Wang J.Meng L.Deng Y.Li Y.Lei A. Angew. Chem. Int. Ed. 2011, 50: 5144 -
39b
Gowrisankar S.Neumann H.Beller M. Angew. Chem. Int. Ed. 2011, 50: 5139 -
40a
Lyons W.Sanford MS. Chem. Rev. 2010, 110: 1147 -
40b
Mkhalid IA.Barnard JH.Marder TB.Murphy JM.Hartwig JF. Chem. Rev. 2010, 110: 890 -
40c
Colby DA.Bergman RG.Ellman JA. Chem. Rev. 2010, 110: 624 -
40d
Daugulis O.Do H.-Q.Shabashov D. Acc. Chem. Res. 2009, 42: 1074 -
40e
Chen X.Engle KM.Wang D.-H.Yu J.-Q. Angew. Chem. Int. Ed. 2009, 48: 5094 -
40f
Ackermann L.Vicente R.Kapdi AR. Angew. Chem. Int. Ed. 2009, 48: 9792 -
40g
Li B.-J.Yang S.-D.Shi Z.-J. Synlett 2008, 949 -
40h
Herrerías CI.Yao X.Li Z.Li C.-J. Chem. Rev. 2007, 107: 2546 -
40i
Alberico D.Scott ME.Lautens M. Chem. Rev. 2007, 107: 174 -
40j
Liu C.Zhang H.Shi W.Lei A. Chem. Rev. 2011, 111: 1780 -
40k
Ashenhurst JA. Chem. Soc. Rev. 2010, 39: 540 -
40l
Nishikata T.Abela AR.Huang S.Lipshutz BH. Angew. Chem. Int. Ed. 2010, 49: 781 -
40m
Sun C.-L.Li B.-J.Shi Z.-J. Chem. Rev. 2011, 111: 1293 -
40n
Yeung CS.Dong VM. Chem. Rev. 2011, 111: 1215 -
41a
Dick AR.Hull KL.Sanford MS. J. Am. Chem. Soc. 2004, 126: 2300 -
41b
Kalyani D.Sanford MS. Org. Lett. 2005, 7: 4149 -
41c
Desai LV.Hull KL.Sanford MS.
J. Am. Chem. Soc. 2004, 126: 9542 -
41d
Desai LV.Malik HA.Sanford MS. Org. Lett. 2006, 8: 1141 -
41e
Reddy BVS.Reddy LR.Corey EJ. Org. Lett. 2006, 8: 3391 -
41f
Hull KL.Lanni EL.Sanford MS. J. Am. Chem. Soc. 2006, 128: 14047 -
41g
Wang G.-W.Yuan T.-T.Wu X.-L. J. Org. Chem. 2008, 73: 4717 -
41h
Fu Y.Li Z.Liang S.Guo Q.-X.Liu L. Organometallics 2008, 27: 3736 -
41i
Wang D.-H.Hao X.-S.Wu D.-F.Yu J.-Q. Org. Lett. 2006, 8: 3387 - 42
Giri R.Liang J.Lei J.-G.Li J.-J.Wang D.-H.Chen X.Naggar IC.Guo C.Foxman BM.Yu J.-Q. Angew. Chem. Int. Ed. 2005, 44: 7420 - 43
Chen X.Hao X.-S.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 6790 - For the direct benzoxylation of the arene C-H bond, other than acetoxylation, see:
-
44a
Dick AR.Kampf JW.Sanford MS. J. Am. Chem. Soc. 2005, 127: 12790 -
44b
Racowski JM.Dick AR.Sanford MS. J. Am. Chem. Soc. 2009, 131: 10974 -
44c
Sun C.-L.Liu J.Wang Y.Zhou X.Li B.-J.Shi Z.-J. Synlett 2011, 883 - 45
Jia X.Zhang S.Wang W.Luo F.Cheng J. Org. Lett. 2009, 11: 3120 - 46
Ye Z.Wang W.Luo F.Zhang S.Cheng J. Org. Lett. 2009, 11: 3974 - 47
Zhang S.Luo F.Wang W.Hu M.Jia X.Cheng J. Tetrahedron Lett. 2010, 51: 3317 - 48
Wang W.Luo F.Zhang S.Cheng J. J. Org. Chem. 2010, 75: 2415 - 49
Wang W.Pan C.Chen F.Cheng J. Chem. Commun. 2011, 47: 3978 -
50a
Dhimitruka I.SantaLucia J. Org. Lett. 2006, 8: 47 -
50b
Fife WK.Xin Y. J. Am. Chem. Soc. 1987, 109: 1278 -
50c
Kuo C.-S.Jwo J.-J. J. Org. Chem. 1992, 57: 1991 -
50d
Adkins H.Thompson QE. J. Am. Chem. Soc. 1949, 71: 2242