Progress on Decarboxylation and Hydroxylation of Carboxylic Acids

doi:10.6023/cjoc202306005

Abstract

Carboxylic acids are inexpensive, readily available, stable and functionally diverse molecules, and alcohols are used as important functional molecules in a variety of applications. Therefore, decarboxylative hydroxylation of carboxylic acid provides a direct and rapid route to important alcohol molecules from stabilized and easily obtainable carboxylic acid feedstocks through benign single carbon excision reductions, which is a very important and useful transformation in organic synthesis and nature. The research progress on decarboxylative hydroxylation reactions to obtain the corresponding primary, secondary and tertiary alcohols, mainly in terms of transition metal catalysis, photocatalysis, electrocatalysis and other types of catalysis, is highlighted with an emphasis on the possible mechanisms and applicable scope of these different reactions. Among them, transition metal catalysis emerged earlier and produced tertiary alcohols in higher yields, but with less universal substrates, whereas photocatalysis is a mild reaction with low environmental pollution and is suitable for the production of primary, secondary and tertiary alcohols.

Key words: carboxylic acid, decarboxylation and hydroxylation, alcohol, transition metal catalysis, photocatalysis

Cite this article

Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 23

Scheme 1. Oxidative decarboxylation and mechanism of pivalic acid with oxygen catalyzed by Mn(III)

Scheme 2. Silver(II) catalyzed oxidative decarboxylation and mechanism of carboxylic acids

Scheme 3. Cerium(IV) catalyzed oxidative decarboxylation of substituted phenylacetic acids

Scheme 4. Oxidative decarboxylation of α-aryl carboxylic acids catalyzed by iron porphyrin-iodosylbenzene system

Scheme 5. Oxidative decarboxylation of α-aryl carboxylic acids catalyzed by MIII(tpp)Cl/Bu4NIO4

Scheme 6. Oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by Mn(III)-salophen

Scheme 7. Oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by [Mn(NH2TPP)-CMP]

Scheme 8. CAN mediated decarboxylative hydroxylation and mechanism of N-aryl-γ-lactam-carboxylic acids

Scheme 9. Synthesis of benzyl alcohols and its reaction mechanism

Scheme 10. AgNO3/K2S2O8-mediated decarboxylative nitration and hydroxylation and mechanism of carboxylic acids

Scheme 11. Decarboxylative oxygenation of pivalic acids catalyzed by cerium(IV) carboxylate

Scheme 12. Decarboxylative hydroxylation and mechanism of carboxylic acids with N-hydroxypyridine-2-thione

Scheme 13. Decarboxylative photooxygenation and mechanism of free carboxylic acids mediated by acridine

Scheme 14. Visible light-induced decarboxylative hydroxylation of carboxylic acids with N-hydroxy-4-methylthiazolidine-2-thione

Scheme 15. Photocatalytic decarboxylative hydroxylation and mechanism of carboxylic acid mediated by catalyst MesAcrClO4 and molecular oxygen

Scheme 16. Decarboxylative oxidation and mechanism of arylacetic acids under photoredox catalysis

Scheme 17. Synthesis and reaction mechanism of aliphatic alcohol under photoredox catalysis

Scheme 18. Decarboxylative oxygenation and mechanism of carboxylic acids catalyzed by cerium(IV) carboxylate

Scheme 19. Photocatalytic decarboxylative hydroxylation of different sp3 carbon-bearing carboxylic acids

Scheme 20. Decarboxylative hydroxylation and mechanism of benzylic carboxylic acids with water as nucleophilea

Scheme 21. Electrocatalyzed decarboxylative hydroxylation and mechanism of carboxylic acids

Scheme 22. Oxidative decarboxylation-β-iodination and mechanism of α-amino acids

Scheme 23. Decarboxylative hydroxylation and mechanism mediated by salicylate hydroxylase

References 58

[1]	(a) Devine, P. N.; Howard, R. M.; Kumar, R.; Thompson, M. P.; Truppo, M. D.; Turner, N. Nat. Rev. Chem. 2018, 2, 409. doi: 10.1038/s41570-018-0055-1
	(b) Simić, S.; Zukić, E.; Schmermund, L.; Faber, K.; Winkler, C. K.; Kroutil, W. Chem. Rev. 2022, 122, 1052. doi: 10.1021/acs.chemrev.1c00574
[2]	(a) Schwartz, R. E.; Helms, G. L.; Bolessa, E. A.; Wilson, K. E.; Giacobbe, R. A.; Tkacz, J. S.; Bills, G. F.; Liesch, J. M.; Zink, D. L.; Curotto, J. E.; Pramanik, B.; Onishi, J. C. Tetrahedron 1994, 50, 1675. doi: 10.1016/S0040-4020(01)80843-7
	(b) Coutrot, P.; Claudel, S.; Didierjean, C.; Grison, C. Bioorg. Med. Chem. Lett. 2006, 16, 417. doi: 10.1016/j.bmcl.2005.09.068
	(c) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677. doi: 10.1021/ja00052a096
	(d) Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139. doi: 10.1021/ja00084a062
[3]	Xu, S.-C.; Zhu, S.-J.; Bi, L.-W.; Chen, Y.-X.; Wang, J.; Lu, Y.-J.; Gu, Y.; Zhao, Z.-D. Chin. Chem. Lett. 2017, 28, 575. doi: 10.1016/j.cclet.2016.11.020
[4]	Xu, X.-Z.; Zhang, F.; Huang, S.; Zhang, Z.-Q.; Ke, F. Chin. J. Org. Chem. 2020, 40, 2912 (in Chinese). doi: 10.6023/cjoc202005004
	(许秀枝, 张帆, 黄胜, 张志强, 柯方, 有机化学, 2020, 40, 2912.)
[5]	Wang, Y.-L.; Huang, Y.-B.; Xi, H.-P. Organic Chemistry, Chemical Industry Press, Beijing, 2020, p. 1 (in Chinese).
	(王永丽, 黄永斌, 席会平, 有机化学, 化学工业出版社, 北京, 2020, p. 1.)
[6]	(a) Totah, R. A.; Hanzlik, R. P. J. Am. Chem. Soc. 2002, 124, 10000. doi: 10.1021/ja020559u
	(b) Wo, J.; Kong, D.; Brock, N. L.; Xu, F.; Zhou, X.; Deng, Z.; Lin, S. ACS Catal. 2016, 6, 2831. doi: 10.1021/acscatal.6b00154
	(c) Zhang, Z.; Xie, S.; Cheng, B.; Zhai, H.; Li, Y. J. Am. Chem. Soc. 2019, 141, 7147. doi: 10.1021/jacs.9b02362
[7]	(a) Beckett, A. H.; Rowland, M. J. Pharm. Pharmacol. 1965, 17, 628. doi: 10.1111/j.2042-7158.1965.tb07575.x
	(b) Dring, L. G.; Smith, R. L.; Williams, R. T. Biochem. J. 1970, 116, 425. doi: 10.1042/bj1160425
	(c) El-Haj, B. M.; Ahmed, S. B. M. Molecules 2020, 25, 1937. doi: 10.3390/molecules25081937
[8]	(a) Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. doi: 10.1016/S0040-4039(00)61242-X
	(b) Komuro, M.; Higuchi, T.; Hirobe, M. Bioorg. Med. Chem. 1995, 3, 55.
[9]	(a) Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030. doi: 10.1039/c1cs15093f
	(b) Xuan, J.; Zhang, Z.; Xiao, W. Angew. Chem., Int. Ed. 2015, 54, 15632. doi: 10.1002/anie.v54.52
	(c) Moon, P. J.; Lundgren, R. J. ACS Catal. 2020, 10, 1742. doi: 10.1021/acscatal.9b04956
	(d) Zeng, Z.; Feceu, A.; Sivendran, N.; Gooßen, L. J. Adv. Synth. Catal. 2021, 363, 2678. doi: 10.1002/adsc.v363.11
	(e) Varenikov, A.; Shapiro, E.; Gandelman, M. Chem. Rev. 2021, 121, 412. doi: 10.1021/acs.chemrev.0c00813
[10]	(a) Sakakibara, Y.; Ito, E.; Fukushima, T.; Murakami, K.; Itami, K. Chem.-Eur. J. 2018, 24, 9254. doi: 10.1002/chem.v24.37
	(b) Kong, D.; Moon, P. J.; Bsharat, O.; Lundgren, R. J. Angew. Chem., Int. Ed. 2020, 59, 1313. doi: 10.1002/anie.v59.3
	(c) Nguyen, V. T.; Nguyen, V. D.; Haug, G. C.; Vuong, N. T. H.; Dang, H. T.; Arman, H. D.; Larionov, O. V. Angew. Chem., Int. Ed. 2020, 59, 7921. doi: 10.1002/anie.v59.20
	(d) Narobe, R.; Murugesan, K.; Schmid, S.; König, B. ACS Catal. 2022, 12, 809. doi: 10.1021/acscatal.1c05077
	(e) Li, Q. Y.; Gockel, S. N.; Lutovsky, G. A.; DeGlopper, K. S.; Baldwin, N. J.; Bundesmann, M. W.; Tucker, J. W.; Bagley, S. W.; Yoon, T. P. Nat. Chem. 2022, 14, 94. doi: 10.1038/s41557-021-00834-8
[11]	(a) Senaweera, S.; Cartwright, K. C.; Tunge, J. A. J. Org. Chem. 2019, 84, 12553. doi: 10.1021/acs.joc.9b02092
	(b) Martínez, Á. M.; Hayrapetyan, D.; van Lingen, T.; Dyga, M.; Gooßen, L. J. Nat. Commun. 2020, 11, 4407. doi: 10.1038/s41467-020-18275-1
	(c) Maeda, B.; Sakakibara, Y.; Murakami, K.; Itami, K. Org. Lett. 2021, 23, 5113. doi: 10.1021/acs.orglett.1c01645
[12]	Anderson, J. M.; Kochi, J. K. J. Am. Chem. Soc. 1970, 92, 2450. doi: 10.1021/ja00711a041
[13]	DeKlein, W. J.; Kooyman, E. C. J. Catal. 1965, 4, 626. doi: 10.1016/0021-9517(65)90170-3
[14]	Anderson, J.; Kochi, J. K. J. Org. Chem. 1970, 35, 986. doi: 10.1021/jo00829a026
[15]	Trahanovsky, W. S.; Cramer, J.; Brixius, D. W. J. Am. Chem. Soc. 1974, 96, 1077. doi: 10.1021/ja00811a022
[16]	Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. doi: 10.1016/S0040-4039(00)61242-X
[17]	(a) Kobayashi, H.; Higuchi, T.; Kaizu, Y.; Osada, H.; Aoki, M. Bull. Chem. Soc. Jpn. 1975, 48, 3137. doi: 10.1246/bcsj.48.3137
	(b) van der Made, A. W.; Hoppenbrouwer, E. J. H.; Nolte, R. J. M.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1988, 107, 15. doi: 10.1002/recl.v107:1
[18]	Tangestaninejad, S.; Mirkhani, V. J. Chem. Res., Synop. 1998, 820.
[19]	Mirkhani, V.; Tangestaninejad, S.; Moghadam, M.; Moghbel, M. Bioorg. Med. Chem. 2004, 12, 903.
[20]	Mirkhani, V.; Tangestaninejad, S.; Moghadam, M.; Karimian, Z. Bioorg. Med. Chem. Lett. 2003, 13, 3433. doi: 10.1016/S0960-894X(03)00749-2
[21]	Haldar, P.; Ray, J. K. Tetrahedron Lett. 2008, 49, 3659. doi: 10.1016/j.tetlet.2008.03.147
[22]	(a) Nair, V.; Panicker, S. B.; Nair, L. G.; George, T. G.; Augustine, A. Synlett 2003, 156.
	(b) Nair, V.; Balagopal, L.; Rajan, R.; Mathew, J. Acc. Chem. Res. 2004, 37, 21. doi: 10.1021/ar030002z
	(c) Nair, V.; Deepthi, A. Chem. Rev. 2007, 107, 1862. doi: 10.1021/cr068408n
	(d) Fujioka, H.; Hirose, H.; Ohba, Y.; Murai, K.; Nakahara, K.; Kita, Y. Tetrahedron 2007, 63, 625. doi: 10.1016/j.tet.2006.11.004
[23]	Yu, Q.; Zhou, D. L.; Liu, Y. Y.; Huang, X. J.; Song, C. L.; Ma, J. J.; Li, J. K. Org. Lett. 2023, 25, 47. doi: 10.1021/acs.orglett.2c03741
[24]	(a) Wang, Z.; Zhu, L.; Yin, F.; Su, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 4258. doi: 10.1021/ja210361z
	(b) Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401. doi: 10.1021/ja3048255
	(c) Liu, C.; Wang, X.; Li, Z.; Cui, L.; Li, C. J. Am. Chem. Soc. 2015, 137, 9820. doi: 10.1021/jacs.5b06821
	(d) Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330. doi: 10.1021/ja306638s
	(e) Cui, L.; Chen, H.; Liu, C.; Li, C. Org. Lett. 2016, 18, 2188. doi: 10.1021/acs.orglett.6b00802
	(f) Tan, X.; Song, T.; Wang, Z.; Chen, H.; Cui, L.; Li, C. Org. Lett. 2017, 19, 1634. doi: 10.1021/acs.orglett.7b00439
	(g) Dong, Y.; Wang, Z.; Li, C. Nat. Commun. 2017, 8, 277. doi: 10.1038/s41467-017-00376-z
	(h) Patel, N. R.; Flowers, R. A. J. Org. Chem. 2015, 80, 5834. doi: 10.1021/acs.joc.5b00826
	(l) Zhu, Y.; Li, X.; Wang, X.; Huang, X.; Shen, T.; Zhang, Y.; Sun, X.; Zou, M.; Song, S.; Jiao, N. Org. Lett. 2015, 17, 4702. doi: 10.1021/acs.orglett.5b02155
	(j) Tan, X.; Liu, Z.; Shen, H.; Zhang, P.; Zhang, Z.; Li, C. J. Am. Chem. Soc. 2017, 139, 12430. doi: 10.1021/jacs.7b07944
[25]	(a) Gooßen, L. J.; Linder, C.; Rodríguez, N.; Lange, P. P.; Fromm, A. Chem. Commun. 2009, 46, 7173.
	(b) Gooßen, L. J.; Rodríguez, N.; Linder, C.; Lange, P. P.; Fromm, A. ChemCatChem 2010, 2, 430. doi: 10.1002/cctc.v2:4
	(c) Li, Y.; Ge, L.; Muhammad, M. T.; Bao, H. Synthesis 2017, 49, 5263. doi: 10.1055/s-0036-1590935
	(d) Jian, W.; Ge, L.; Jiao, Y.; Qian, B.; Bao, H. Angew. Chem., Int. Ed. 2017, 56, 3650. doi: 10.1002/anie.v56.13
[26]	Thorpe, W. G.; Kochi, J. K. J. Inorg. Nucl. Chem. 1971, 33, 3958. doi: 10.1016/0022-1902(71)80307-X
[27]	Kamijo, S.; Amaoka, Y.; Inoue, M. Tetrahedron Lett. 2011, 52, 4654. doi: 10.1016/j.tetlet.2011.06.118
[28]	Patel, N. R.; Flowers, R. A. J. Org. Chem. 2015, 80, 5834. doi: 10.1021/acs.joc.5b00826
[29]	Jayakanthan, K.; Madhusudanan, K. P.; Vankar, Y. D. Tetrahedron 2004, 60, 397. doi: 10.1016/j.tet.2003.11.013
[30]	Keith, D. J.; Townsend, S. D. Carbohydr. Res. 2017, 442, 20. doi: 10.1016/j.carres.2017.02.005
[31]	Phae-nok, S.; Kuhakarn, C.; Leowanawat, P.; Reutrakul, V.; Soorukram, D. Synlett 2022, 33, 1323. doi: 10.1055/a-1792-7169
[32]	Sheldon, R. A.; Kochi, J. K. J. Am. Chem. Soc. 1968, 90, 6688. doi: 10.1021/ja01026a022
[33]	(a) Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1984, 242.
	(b) Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. doi: 10.1016/S0040-4020(01)97173-X
	(c) Liu, C.; Wang, X.; Li, Z.; Cui, L.; Li, C. J. Am. Chem. Soc. 2015, 137, 9820. doi: 10.1021/jacs.5b06821
[34]	Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413. doi: 10.1021/cr00097a001
[35]	Barton, D. H. R.; Gero, S. D.; Holliday, P.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron 1998, 54, 6751. doi: 10.1016/S0040-4020(98)00337-8
[36]	Barton, D. H. R.; Zard, S. Z. Pure Appl. Chem. 1986, 58, 675. doi: 10.1351/pac198658050675
[37]	Okada, K.; Okubo, K.; Oda, M. Tetrahedron Lett. 1992, 33, 83. doi: 10.1016/S0040-4039(00)77679-9
[38]	Song, H.-T.; Ding, W.; Zhou, Q.-Q.; Liu, J.; Lu, L.-Q.; Xiao, W.-J. J. Org. Chem. 2016, 81, 7250. doi: 10.1021/acs.joc.6b01360
[39]	Wang, G.-Z.; Shang, R.; Cheng, W.-M.; Fu, Y. Org. Lett. 2015, 17, 4830. doi: 10.1021/acs.orglett.5b02392
[40]	(a) Ohkubo, K.; Suga, K.; Morikawa, K.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 12850. doi: 10.1021/ja036645r
	(b) Kotani, H.; Ohkubo, K.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 15999. doi: 10.1021/ja048353b
[41]	(a) Cassani, C.; Bergonzini, G.; Wallentin, C.-J. Org. Lett. 2014, 16, 4228. doi: 10.1021/ol5019294
	(b) Chinzei, T.; Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. RSC Adv. 2015, 5, 21297. doi: 10.1039/C5RA01826A
	(c) Wu, X.-X.; Meng, C.-N.; Yuan, X.-Q.; Jia, X.-T.; Qian, X.-H.; Ye, J.-X. Chem. Commun. 2015, 51, 11864. doi: 10.1039/C5CC04527D
	(d) Wang, K.; Meng, L.-G.; Zhang, Q.; Wang, L. Green Chem. 2016, 18, 2864. doi: 10.1039/C5GC02550H
[42]	(a) Su, Y.-J.; Zhang, L.-R.; Jiao, N. Org. Lett. 2011, 13, 2168. doi: 10.1021/ol2002013
	(b) Yi, H.; Bian, C.-L.; Hu, X.; Niu, L.-B.; Lei, A. Chem. Commun. 2015, 51, 14046. doi: 10.1039/C5CC06015J
	(c) Jung, J.; Kim, J.; Park, G.; You, Y.-M.; Cho, E. J. Adv. Synth. Catal. 2016, 358, 74. doi: 10.1002/adsc.v358.1
	(d) Wang, H.-M.; Lu, Q.-Q.; Qian, C.H.; Liu, C.; Liu, W.; Chen, K.; Lei, A. Angew. Chem., Int. Ed. 2016, 55, 1094. doi: 10.1002/anie.v55.3
[43]	Sakakibara, Y.; Cooper, P.; Murakami, K.; Itami, K. Chem.-Asian J. 2018, 13, 2410. doi: 10.1002/asia.v13.17
[44]	(a) Ohkubo, K.; Suga, K.; Morikawa, K.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 12850. doi: 10.1021/ja036645r
	(b) Ohkubo, K.; Mizushima, K.; Iwata, R.; Souma, K.; Suzuki, N. Fukuzumi, S. Chem. Commun. 2010, 46, 601. doi: 10.1039/B920606J
	(c) Yi, H.; Bian, C.; Hu, X.; Niu, L.; Lei, A. Chem. Commun. 2015, 51, 14046. doi: 10.1039/C5CC06015J
[45]	Zheng, C.; Wang, Y.-T.; Xu, Y.-R.; Chen, Z.; Chen, G.-Y.; Liang, S.-H. Org. Lett. 2018, 20, 4824. doi: 10.1021/acs.orglett.8b01885
[46]	Shirase, S.; Tamaki, S.; Shinohara, K.; Hirosawa, K.; Tsurugi, H.; Satoh, T.; Mashima, K. J. Am. Chem. Soc. 2020, 142, 5668. doi: 10.1021/jacs.9b12918
[47]	Sheldon, R. A.; Kochi, J. K. J. Am. Chem. Soc. 1968, 90, 6688. doi: 10.1021/ja01026a022
[48]	Yatham, V. R.; Bellotti, P.; König, B. Chem. Commun. 2019, 55, 3489. doi: 10.1039/C9CC00492K
[49]	(a) Partenheimer, W. J. Mol. Catal. A: Chem. 2003, 206, 105. doi: 10.1016/S1381-1169(03)00407-2
	(b) Hermans, I.; Peeters, J.; Vereecken, L.; Jacobs, P. A. ChemPhysChem 2007, 8, 2678. doi: 10.1002/cphc.v8:18
	(c) Wang, X.; Cao, X.; Hu, X.; Li, G.; Zhu, L.; Hu, C. J. Mol. Catal. A: Chem. 2012, 357, 1. doi: 10.1016/j.molcata.2011.12.005
[50]	Khan, S. N.; Zaman, M. K.; Li, R.; Sun, Z. J. Org. Chem. 2020, 85, 5019. doi: 10.1021/acs.joc.0c00312
[51]	Li, P.; Zbieg, J. R.; Terrett, J. A. ACS Catal. 2021, 11, 10997. doi: 10.1021/acscatal.1c03251
[52]	Coleman, J. P.; Lines, R.; Utley, J. H. P.; Weedon, B. C. L. J. Chem. Soc., Perkin Trans. 2 1974, 1064.
[53]	Xiang, J.; Shang, M.; Kawamata, Y.; Lundberg, H.; Reisberg, S.H.; Chen, M.; Mykhailiuk, P.; Beutner, G.; Collins, M. R.; Davies, A.; Del Bel, M.; Gallego, G. M.; Spangler, J. E.; Starr, J.; Yang, S.; Blackmond, D. G.; Baran, P. S. Nature 2019, 573, 398. doi: 10.1038/s41586-019-1539-y
[54]	(a) Boto, A.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1999, 40, 5945. doi: 10.1016/S0040-4039(99)01180-6
	(b) Boto, A.; Hernández, R.; Suárez, E. Tetrahedron Lett. 2000, 41, 2495. doi: 10.1016/S0040-4039(00)00188-X
	(c) Boto, A.; Hernández, R.; Suárez, E. J. Org. Chem. 2000, 65, 4930. doi: 10.1021/jo000356t
[55]	Yamamoto, S.; Katagiri, M.; Maeno, H.; Hayaiahi, O. J. Biol. Chem. 1965, 240, 3408. doi: 10.1016/S0021-9258(18)97232-7
[56]	Katagiri, M.; Maeno, H.; Yamamoto, S.; Hayaishi, O.; Kitano, T.; Oae, S. J. Biol. Chem. 1965, 240, 3414. doi: 10.1016/S0021-9258(18)97233-9
[57]	Katagiri, M.; Takemori, S.; Suzuki, K.; Yasuda, H. J. Biol. Chem. 1966, 241, 5675. doi: 10.1016/S0021-9258(18)96397-0
[58]	Uemura, T.; Kita, A.; Watanabe, Y.; Adachi, M.; Kuroki, R.; Morimoto, Y. Biochem. Biophys. Res. Commun. 2016, 469, 158. doi: 10.1016/j.bbrc.2015.11.087

羧酸脱羧羟基化反应研究进展