Phosphorylation of Carboxylic Acids and Their Derivatives with P(O)–H Compounds Forming P(O)–C Bonds

Tieqiao Chen; Qihang Tan; Xue Liu; Long Liu; Tianzeng Huang; Li-Biao Han

doi:10.1055/s-0040-1707286

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(01): 95-106
DOI: 10.1055/s-0040-1707286

short review

Phosphorylation of Carboxylic Acids and Their Derivatives with P(O)–H Compounds Forming P(O)–C Bonds

Tieqiao Chen∗

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chem, Hainan University, Haikou, 570228, P. R. of China eMail: chentieqiao@hnu.edu.cn

,

Qihang Tan

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chem, Hainan University, Haikou, 570228, P. R. of China eMail: chentieqiao@hnu.edu.cn

,

Xue Liu

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chem, Hainan University, Haikou, 570228, P. R. of China eMail: chentieqiao@hnu.edu.cn

,

Long Liu

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chem, Hainan University, Haikou, 570228, P. R. of China eMail: chentieqiao@hnu.edu.cn

,

Tianzeng Huang

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chem, Hainan University, Haikou, 570228, P. R. of China eMail: chentieqiao@hnu.edu.cn

,

Li-Biao Han∗

^bDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan eMail: libiao-han@aist.go.jp

› Institutsangaben

Abstract

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Abstract

Herein, we highlight advances in the phosphorylation of readily available carboxylic acids and their derivatives forming synthetically important P(O)–sp³C, P(O)–sp²C, and P(O)–spC bonds, with an emphasis on the results demonstrated since 2010. This review examines the challenges associated with the use of this strategy for the synthesis of organophosphorus compounds and details advances in the design of catalytic systems that suppress these problems thus resulting in notable progress. Mechanistic details are discussed where available.

1 Introduction

2 Formation of P(O)–sp³C Bonds

3 Formation of P(O)–sp²C Bonds

4 Formation of P(O)–spC Bonds

5 Outlook and Conclusion

Key words

phosphorylation - carboxylic acids - decarboxylation - decarbonylation - cross coupling

Volltext

Referenzen

References

1a Corbridge DE. C. Phosphorus: Chemistry, Biochemistry and Technology, 6th ed. CRC Press; New York: 2013
1b Quin LD. A Guide to Organophosphorus Chemistry . Wiley Interscience; New York: 2000
1c Monge S, David G. Phosphorus-Based Polymers from Synthesis to Applications . Royal Society of Chemistry; Cambridge: 2014
1d Ni H, Chan WL, Lu Y. Chem. Rev. 2018; 118: 9344
1e Montchamp J.-L. Acc. Chem. Res. 2014; 47: 77
1f Ma YN, Li S.-X, Yang S.-D. Acc. Chem. Res. 2017; 50: 1480
1g Baumgartner T, Réau R. Chem. Rev. 2006; 106: 4681
1h Queffelec C, Petit M, Janvier P, Knight DA, Bujoli B. Chem. Rev. 2012; 112: 3777

For selected examples, see:

2a Jiménez MV, Pérez-Torrente JJ, Bartolomé MI, Oro LA. Synthesis 2009; 1916
2b Casey CP, Paulsen EL, Beuttenmueller EW, Proft BR, Petrovich LM, Matter BA, Powell DR. J. Am. Chem. Soc. 1997; 119: 11817

3 For a review, see: Bhattacharya AK, Thyarajan G. Chem. Rev. 1981; 81: 415

4a Hirao T, Masunaga T, Ohshiro Y, Agawa T. Tetrahedron Lett. 1980; 21: 3595
4b Hirao T, Masunaga T, Yamada N, Ohshiro Y, Agawa T. Bull. Chem. Soc. Jpn. 1982; 55: 909

For selected examples, see:

5a Liao LL, Gui YY, Zhang XB, Shen G, Liu HD, Zhou WJ, Li J, Yu DG. Org. Lett. 2017; 19: 3735
5b Fu WC, So CM, Kwong FY. Org. Lett. 2015; 17: 5906
5c Gelman LJ. D, Buchwald SL. Org. Lett. 2003; 5: 2315
5d Zhang H.-Y, Sun M, Ma Y.-N, Tian Q.-P, Yang S.-D. Org. Biomol. Chem. 2012; 10: 9627

For selected reviews, see:

6a Chen T, Zhang J.-S, Han L.-B. Dalton Trans. 2016; 45: 1843
6b Xu Q, Han L.-B. J. Organomet. Chem. 2011; 696: 130
6c Schwan AL. Chem. Soc. Rev. 2004; 33: 218
6d Chen T, Han L.-B. Synlett 2015; 26: 1153
6e Demmer CS, Krogsgaard-Larsen N, Bunch L. Chem. Rev. 2011; 111: 7981

For selected examples, see:

6f Yang J, Xiao J, Chen T, Yin S.-F, Han L.-B. Chem. Commun. 2016; 52: 12233
6g Yang J, Chen T, Han L.-B. J. Am. Chem. Soc. 2015; 137: 1782
6h Yang J, Xiao J, Chen T, Han L.-B. J. Org. Chem. 2016; 81: 3911
6i Zhang J.-S, Chen T, Zhou Y, Yin S.-F, Han L.-B. Org. Lett. 2018; 20: 6746
6j Zhuang R, Xu J, Cai Z, Tang G, Fang M, Zhao Y. Org. Lett. 2011; 13: 2110
6k Miao W, Gao Y, Li X, Gao Y, Tang G, Zhao Y. Adv. Synth. Catal. 2012; 354: 2659
6l Zhang J.-S, Chen T, Yang J, Han L.-B. Chem. Commun. 2015; 51: 7540

For selected reviews, see:

7a Rodriguez N, Gooßen LJ. Chem. Soc. Rev. 2011; 40: 5030
7b Bonesi SM, Fagnoni M. Chem. Eur. J. 2010; 16: 13572
7c Patra T, Maiti D. Chem. Eur. J. 2017; 23: 7382
7d Dzik WI, Lange PP, Gooßen LJ. Chem. Sci. 2012; 3: 2671
7e Guo L, Rueping M. Acc. Chem. Res. 2018; 51: 51185
7f Dermenci A, Dong G. Sci. China Chem. 2013; 56: 685
7g Guo L, Rueping M. Chem. Eur. J. 2018; 24: 7794
7h Cai X.-H, Yang M, Xie B. Curr. Org. Chem. 2018; 22: 1906
7i Perry GJ. P, Larrosa I. Eur. J. Org. Chem. 2017; 2017: 3517
7j Hu X.-Q, Liu Z.-K, Hou Y.-X, Gao Y. iScience 2020; 23: 101266

8 In 2018, Hosseinian and co-workers outlined the advances in the decarboxylation of carboxylic acids forming P(O)–C bonds, see: Hosseinian A, Nasab FA. H, Ahmadi S, Rahmani Z, Vessally E. RSC Adv. 2018; 8: 26383

For coordination of P(O)–H compounds with metals, see:

9a Shaikh TM, Weng C.-M, Hong F.-E. Coord. Chem. Rev. 2012; 256: 771
9b Wang X.-B, Goto M, Han L.-B. Chem. Eur. J. 2014; 20: 3631
9c Cano I, Chapman AM, Urakawa A, van Leeuwen WN. M. J. Am. Chem. Soc. 2014; 136: 2520
9d Schröder F, Tugny C, Salanouve E, Clavier H, Giordano L, Moraleda D, Gimbert Y, Mouriès-Mansuy V, Goddard J.-P, Fensterbank L. Organometallics 2014; 33: 4051

10 Jin S, Haug GC, Nguyen VT, Flores-Hansen C, Arman HD, Larionov OV. ACS Catal. 2019; 9: 9764

For a review, see:

11a Rahman M, Mukherjee A, Kovalev IS, Kopchuk DS, Zyryanov GV, Tsurkan MV, Majee A, Ranu BC, Charushin VN, Chupakhin ON, Santra S. Adv. Synth. Catal. 2019; 361: 2161

For selected examples, see:

11b Bi H.-P, Zhao L, Liang Y.-M, Li C.-J. Angew. Chem. Int. Ed. 2009; 48: 792
11c Bi H.-P, Chen W.-W, Liang Y.-M, Li C.-J. Org. Lett. 2009; 11: 3246
11d Zhang C, Seidel D. J. Am. Chem. Soc. 2010; 132: 1798
11e Guo J, Xie Y, Wu Q.-L, Zeng W.-T, Chan AS. C, Weng J, Lu G. RSC Adv. 2018; 8: 16202

12 Hu J, Zhao N, Yang B, Wang G, Guo L.-N, Liang Y.-M, Yang S.-D. Chem. Eur. J. 2011; 17: 5516
13 In 2013, Boto and co-workers reported the stereoselective reaction of C4-chiral proline derivatives with P(OMe)₃ through one-pot two-step decarboxylation/phosphorylation process, five examples were demonstrated, see: Miguelez-Ramos J, Batchu VR, Boto A. Eur. J. Org. Chem. 2013; 846
14 Yang D, Zhao D, Mao L, Wang L, Wang R. J. Org. Chem. 2011; 76: 6426

For reviews on A³ coupling, see:

15a Peshkov VA, Pereshivko OP, der Eycken EV. V. Chem. Soc. Rev. 2012; 41: 3790
15b Rokade BV, Barker J, Guiry PJ. Chem. Soc. Rev. 2019; 48: 4766
15c Nasrollahzadeh M, Sajjadi M, Ghorbannezhad F, Sajadi SM. Chem. Rec. 2018; 18: 1409

16 It should be noted that the aldehyde-induced decarboxylative phosphorylation of l-proline with P(OEt)₃ was achieved with the use of cerium(IV) oxide as a catalyst, similar products were obtained, see: Firouzabadi H, Iranpoor N, Ghaderi A, Ghavami M. Tetrahedron Lett. 2012; 53: 5515
17 Kaboudin B, Karami L, Kato J.-y, Aoyama H, Yokomatsu T. Tetrahedron Lett. 2013; 54: 4872
18 Wang X, Zhang C, Shen R, Han L.-B. J. Org. Chem. 2020;

19a Sartori P, Mosler G. Phosphorus Sulfur 1980; 8: 115
19b Kobayashi T, Eda T, Tamura H, Ishibashi H. J. Org. Chem. 2002; 67: 3156

20 Bew SP, Brimage RA, Hughes DL, Legentil L, Sharma SV, Wilson MA. J. Org. Chem. 2007; 72: 2655

21a Kurosawa MB, Isshiki R, Muto K, Yamaguchi J. J. Am. Chem. Soc. 2020; 142: 7386

Despite the structural similarity, H-phosphonates, H-phosphinates, and secondary H-phosphine oxides usually show different reactivity in transition-metal catalysis. For a selected example on related studies, see:

21b Chen T, Zhao C.-Q, Han L.-B. J. Am. Chem. Soc. 2018; 140: 3139

22 Zhou M, Zhou Y, Song Q. Chem. Eur. J. 2015; 21: 10654 correction: Chem. Eur. J. 2015, 21, 11627
23 Chen X, Chen X, Li X, Qu C, Qu L, Bi W, Sun K, Zhao Y. Tetrahedron 2017; 73: 2439
24 Zhou Y, Zhou M, Chen M, Su J, Du J, Song Q. RSC Adv. 2015; 5: 103977
25 Zhou M, Chen M, Zhou Y, Yang K, Su J, Du J, Song Q. Org. Lett. 2015; 17: 1786
26 Zhang P, Zhang L, Gao Y, Xu J, Fang H, Tang G, Zhao Y. Chem. Commun. 2015; 51: 7839
27 Zeng Y.-F, Tan D.-H, Lv W.-X, Li Q, Wang H. Eur. J. Org. Chem. 2015; 2015: 4335

For selected examples, see:

28a Gooßen LJ, Deng G, Levy LM. Science 2006; 313: 662
28b Tang J, Biafora A, Gooßen LJ. Angew. Chem. Int. Ed. 2015; 54: 13130
28c Myers AG, Tanaka D, Mannion MR. J. Am. Chem. Soc. 2002; 124: 11250
28d Kan J, Huang S, Lin J, Zhang M, Su W. Angew. Chem. Int. Ed. 2015; 54: 2199
28e Becht J.-M, Drian CL. J. Org. Chem. 2011; 76: 6327
28f Zhang Y, Mainolfi N. Chem. Sci. 2012; 3: 3196
28g Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194
28h Bhadra S, Dzik WI, Gooßen LJ. J. Am. Chem. Soc. 2012; 134: 9938
28i Drapeau MP, Bahri J, Lichte D, Gooßen LJ. Angew. Chem. Int. Ed. 2019; 58: 892
28j Li J, Bi X, Wang H, Xiao J. Asian J. Org. Chem. 2014; 3: 1113

29 Liu C, Ji C.-L, Zhou T, Hong X, Szostak M. Org. Lett. 2019; 21: 9256
30 Zhang J.-S, Chen T, Han L.-B. Eur. J. Org. Chem. 2020; 2020: 1148
31 Liu C, Szostak M. Angew. Chem. Int. Ed. 2017; 56: 12718
32 Xu Y, Wang B, Jiang J, Yu H, Fu Y. J. Org. Chem. 2019; 85: 9474
33 Tong W.-Y, Ly TD, Zhao T.-T, Wu Y.-B, Wang X. Chem. Commun. 2020; 56: 113
34 Isshiki R, Muto K, Yamaguchi J. Org. Lett. 2018; 20: 1150
35 Dong J, Liu L, Ji X, Shang Q, Liu L, Su L, Chen B, Kan R, Zhou Y, Yin S.-F, Han L.-B. Org. Lett. 2019; 21: 3198

For selected examples, see:

36a Han L.-B, Tanaka M. J. Am. Chem. Soc. 1996; 118: 1571
36b Chen T, Zhou Y, Guo C, Han L.-B. Chem. Lett. 2013; 42: 1065
36c Han L.-B, Zhao C.-Q. J. Org. Chem. 2005; 70: 10121
36d Han L.-B, Hua R, Tanaka M. Angew. Chem. Int. Ed. 1998; 37: 94
36e Han L.-B, Zhang C, Yazawa H, Shimada S. J. Am. Chem. Soc. 2004; 126: 5080
36f Kanada J, Tanaka M. Adv. Synth. Catal. 2011; 353: 890
36g Han L.-B, Zhao C.-Q, Onozawa S.-y, Goto M, Tanaka M. J. Am. Chem. Soc. 2002; 124: 3842 ; for a review, see ref. 6b

37 Wu Y, Liu L, Yan K, Xu P, Gao Y, Zhao Y. J. Org. Chem. 2014; 79: 8118
38 Tang L, Wen L, Sun T, Zhang D, Yang Z, Feng C, Wang Z. Asian J. Org. Chem. 2017; 6: 1683
39 For a review, see: Gao Y, Tang G, Zhao Y. Chin. J. Org. Chem. 2018; 38: 62
40 Liu L, Zhou D, Dong J, Zhou Y, Yin S.-F, Han L.-B. J. Org. Chem. 2018; 83: 4190
41 Hu G, Gao Y, Zhao Y. Org. Lett. 2014; 16: 4464
42 Niu M, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2007; 272

43a Chen Y.-R, Duan W.-L. J. Am. Chem. Soc. 2013; 135: 16754
43b Unoh Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 12975

44 Hu G, Zhang Y, Su J, Li Z, Gao Y, Zhao Y. Org. Biomol. Chem. 2015; 13: 8221

45a Mahajna M, Quistad GB, Casida JE. Chem. Res. Toxicol. 1996; 9: 241
45b Krishna H, Caruthers MH. J. Am. Chem. Soc. 2012; 134: 11618
45c Nicolaou KC, Maligres P, Shin J, De Leon E, Rideout D. J. Am. Chem. Soc. 1990; 112: 7825
45d Van derpoorten K, Migaud ME. Org. Lett. 2004; 6: 3461

46a Lera M, Hayes CJ. Org. Lett. 2000; 2: 3873
46b Iorga B, Eymery F, Carmichael D, Savignac P. Eur. J. Org. Chem. 2000; 2000: 3103

47 Wang Y, Gan J, Liu L, Yuan H, Gao Y, Liu Y, Zhao Y. J. Org. Chem. 2014; 79: 3678
48 Yatsumonji Y, Ogata A, Tsubouchi A, Takeda T. Tetrahedron Lett. 2008; 49: 2265

49a Gérard P, Veillard R, Alayrac C, Gaumont A.-C, Evano G. Eur. J. Org. Chem. 2016; 2016: 633
49b Jouvin K, Heimburger J, Evano G. Chem. Sci. 2012; 3: 756

50 Gao Y, Wang G, Chen L, Xu P, Zhao Y, Zhou Y, Han L.-B. J. Am. Chem. Soc. 2009; 131: 7956

Dehydrogenative coupling with P(O)–H compounds is a powerful strategy for the synthesis of organophosphorus compounds. For a review, see ref. 6a. For selected examples, see:

51a Zhu Y, Chen T, Li S, Shimada S, Han L.-B. J. Am. Chem. Soc. 2016; 138: 5825
51b Zhou Y, Yin S, Gao Y, Zhao Y, Goto M, Han L.-B. Angew. Chem. Int. Ed. 2010; 49: 6852
51c Li C, Chen T, Han L.-B. Dalton Trans. 2016; 45: 14893
51d Feng C.-G, Ye M, Xiao KJ, Li S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 9322
51e Ke J, Tang Y, Yin H, Li Y, Cheng Y, Liu C, Lei A. Angew. Chem. Int. Ed. 2015; 54: 6604
51f Zhou Y, Yang J, Chen T, Yin S.-F, Han D, Han L.-B. Bull. Chem. Soc. Jpn. 2014; 87: 400
51g Basle O, Li C.-J. Chem. Commun. 2009; 4124

52a Liu P, Yang J, Li P, Wang L. Appl. Organomet. Chem. 2011; 25: 830
52b Moglie Y, Mascaro E, Gutierrez V, Alonso F, Radivoy G. J. Org. Chem. 2016; 81: 1813
52c Yang J, Chen T, Zhou Y, Yin S, Han L.-B. Chem. Commun. 2015; 51: 3549
52d Liu L, Wu Y, Wang Z, Zhu J, Zhao Y. J. Org. Chem. 2014; 79: 6816
52e Yang J, Chen T, Zhou Y, Yin S.-F, Han L.-B. Organometallics 2015; 34: 5095
52f Wang T, Chen S, Shao A, Gao M, Huang Y, Lei A. Org. Lett. 2015; 17: 118
52g Zhang J.-Q, Chen T, Zhang J.-S, Han L.-B. Org. Lett. 2017; 19: 4692

53 The cleavage of P(O)–H bonds does not required copper catalysts. For direct ligand exchange of P(O)–H compounds with Pd(OAc)₂, see refs 21b and 52e.
54 Li X, Yang F, Wu Y, Wu Y. Org. Lett. 2014; 16: 992
55 It should be noted that the decarboxylative coupling of 3-arylpropynoicaromatic alkynyl carboxylic acids with dialkyl hydrazinylphosphonates forming alkynyl phosphoryl compounds was also achieved through copper catalysis, see: Chen W, Ma D, Hu G, Hong Z, Gao Y, Zhao Y. Synth. Commun. 2016; 46: 1175
56 For a selected example, see: Cao H, Jiang H, Feng H, Kwan JM. C, Liu X, Wu J. J. Am. Chem. Soc. 2018; 140: 16360

57a Liu K, Song C, Lei A. Org. Biomol. Chem. 2018; 16: 2375
57b Tang S, Liu Y, Lei A. Chem 2018; 4: 27
57c Francke R, Little RD. Chem. Soc. Rev. 2014; 43: 2492
57d Yang L, Ma F.-X, Xu F, Li D, Su L, Xu H.-C, Wang C. Chem. Asian J. 2019; 14: 3557
57e Wiebe A, Gieshoff T, Mohle S, Rodrigo E, Zirbes M, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 5594