Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions

Abstract

P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols.

1 Introduction

2 Addition to Alkenes/Alkynes

3 Addition to Other Unsaturated Compounds

4 Coupling with Carbocations

5 Phosphorylation of Aryl C–H Bonds

6 Hirao Reaction

7 P–S, P–O, P–N, or P–F Coupling

8 Conclusions

Key words

mechanism - nucleophile - H-phosphites - H-phosphinates - H-phosphine oxides

Publication History

Received: 17 May 2021

Accepted: 18 May 2021

Accepted Manuscript online:
18 May 2021

Article published online:
17 June 2021

• References

• 1a Maddigan-Wyatt J, Hooper JF. Adv. Synth. Catal. 2021; 363: 924
• 1b Ren W, Yang Q, Yang S.-D. Pure Appl. Chem. 2019; 91: 87
• 1c Henyecz R. Phosphorus, Sulfur Silicon Relat. Elem. 2019; 194: 372
• 1d Brahmachari G. ChemTexts 2015; 1: 15
• 1e Jablonkai E, Keglevich G. Curr. Org. Synth. 2014; 11: 429
• 1f Keglevich G, Henyecz R, Mucsi Z. Molecules 2020; 25: 3897
• 1g Henyecz R, Keglevich G. Curr. Org. Synth. 2019; 16: 523
• 1h Jablonkai E, Keglevich G. Org. Prep. Proced. Int. 2014; 46: 281
• 2a Leeuwen PW. N. M, Cano I, Freixa Z. ChemCatChem 2020; 12: 3982
• 2b Ayad T, Gernet A, Pirat J.-L, Virieux D. Tetrahedron 2019; 75: 4385
• 2c Ackermann L. Synthesis 2006; 1557
• 2d Han L.-B, Chen T. Synlett 2015; 26: 1153
• 2e Chen L, Liu XY, Zou YX. Adv. Synth. Catal. 2020; 362: 1724
• 2f Quint V, Noël-Duchesneau L, Lagadic E, Morlet-Savary F, Lalevée J, Gaumont A, Lakhdar S. Synthesis 2017; 49: 3444
• 3a Salin AV, Islamov DR. Org. Biomol. Chem. 2019; 17: 7293
• 3b Huang T.-Z, Chen T, Saga Y, Han L.-B. Tetrahedron 2017; 73: 7085
• 3c Lenker HK, Richard ME, Reese KP, Carter AF, Zawisky JD, Winter EF, Bergeron TW, Guydon KS, Stockland RA. Jr. J. Org. Chem. 2012; 77: 1378
• 3d Gu Z, Zhou J, Jiang G.-F, Zhou Y.-G. Org. Chem. Front. 2018; 5: 1148
• 3e Zhao D, Wang L, Yang D, Zhang Y, Wang R. Chem. Asian J. 2012; 7: 881
• 3f Fisher HC, Berger O, Gelat F, Montchamp J.-L. Adv. Synth. Catal. 2014; 356: 1199
• 3g Guo S, Huang Z, Liu W, Li S, Yang Y, Cai H. Synlett 2020; 31: 1295
• 4a Peng Z, Zhang Z, Zeng X, Tu Y, Zhao J. Adv. Synth. Catal. 2019; 361: 4489
• 4b Fener BE, Schuler P, Ueberschaar N, Bellstedt P, Gorls H, Krieck S, Westerhausen M. Chem. Eur. J. 2020; 26: 7235
• 4c Trostyanskaya IG, Beletskaya IP. Tetrahedron 2014; 70: 2556
• 4d Huang H, Zhu H, Kang JY. Org. Lett. 2018; 20: 2778
• 4e Wang H, Li Y, Tang Z, Wang S, Zhang H, Cong H, Lei A. ACS Catal. 2018; 8: 10599
• 4f Basiouny MM. I, Dollard DA, Schmidt JA. R. ACS Catal. 2019; 9: 7143
• 4g Chen T, Zhao C.-Q, Han L.-B. J. Am. Chem. Soc. 2018; 140: 3139
• 4h Dobashi N, Fuse K, Hoshino T, Kanada J, Kashiwabara T, Kobata C, Nune SK, Tanaka M. Tetrahedron Lett. 2007; 48: 4669
• 4i Sanji T, Shiraishi K, Kashiwabara T, Tanaka M. Org. Lett. 2008; 10: 2689
• 5a Salin AV, Il’in AV, Faskhutdinov RI, Fayzullin RR. Tetrahedron 2019; 75: 2676
• 5b Guo H, Yoshimura A, Chen T, Saga Y, Han L.-B. Green Chem. 2017; 19: 1502
• 5c Yoshimura A, Saga Y, Sato Y, Ogawa A, Chen T, Han L.-B. Tetrahedron Lett. 2016; 57: 3382
• 5d Zhang JS, Zhang JQ, Chen T, Han L.-B. Org. Biomol. Chem. 2017; 15: 5462
• 6a Lu G, Huangfu X, Wu Z, Tang G, Zhao Y. Adv. Synth. Catal. 2019; 361: 4961
• 6b Ramesh K, Satyanarayana G. Eur. J. Org. Chem. 2019; 2019: 3856
• 6c Chen C, Sun W, Yan Y, Yang F, Wang Y, Zhu YP, Liu L, Zhu B. Adv. Synth. Catal. 2020; 362: 2970
• 7 Yamamoto Y, Fukatsu K, Nishiyama H. Chem. Commun. 2012; 48: 7985
• 8 Qiao B, Cao H.-Q, Huang Y.-J, Zhang Y, Nie J, Zhang F.-G, Ma J.-A. Chin. J. Chem. 2018; 36: 809
• 9a Li C, Yuan JM, Chen W, He Y, Huang J, Huang Y, Xiao Q, Sheng J, Huang C. Chem. Asian J. 2019; 14: 2584
• 9b Huang L, Zhang Z, Jie K, Wang Y, Fu Z, Guo S, Cai H. Org. Chem. Front. 2018; 5: 3548
• 10a Li X, Yang F, Wu Y, Wu Y. Org. Lett. 2014; 16: 992
• 10b Guo H.-M, Zhou Q.-Q, Jiang X, Shi D.-Q, Xiao W.-J. Adv. Synth. Catal. 2017; 359: 4141
• 10c Ruan H, Meng LG, Xu H, Liang Y, Wang L. Org. Biomol. Chem. 2020; 18: 1087
• 10d Hu G, Gao Y, Zhao Y. Org. Lett. 2014; 16: 4464
• 10e Liu LL, Wu Y, Wang Z, Zhu J, Zhao Y. J. Org. Chem. 2014; 79: 6816
• 10f Gérard P, Veillard R, Alayrac C, Gaumont A.-C, Evano G. Eur. J. Org. Chem. 2016; 2016: 633
• 10g Yuan T, Chen F, Lu G.-p. New J. Chem. 2018; 42: 13957
• 10h Wang T, Chen S, Shao A, Gao M, Huang Y, Lei A. Org. Lett. 2015; 17: 118
• 11 Shen R, Yang J, Zhao H, Feng Y, Zhang L, Han L.-B. Chem. Commun. 2016; 52: 11959
• 12a Yang G, Shen C, Quan M, Zhang W. Tetrahedron 2016; 72: 333
• 12b Chen Q, Yan X, Wen C, Zeng J, Huang Y, Liu X, Zhang K. J. Org. Chem. 2016; 81: 9476
• 13a Xiong B, Shen R, Goto M, Yin SF, Han LB. Chem. Eur. J. 2012; 18: 16902
• 13b Zhang M, Jia X, Zhu H, Fang X, Ji C, Zhao S, Han L.-B, Shen R. Org. Biomol. Chem. 2019; 17: 2972
• 13c Xiong B, Wang G, Zhou C, Liu Y, Yang C.-A, Zhang P, Tang K, Zhou Q. J. Organomet. Chem. 2019; 885: 21
• 13d Shen R, Zhang M, Xiao J, Dong C, Han L.-B. Green Chem. 2018; 20: 5111
• 13e Aher YN, Pawar AB. Org. Biomol. Chem. 2019; 17: 7536
• 13f Zhang B, Liu L, Mao S, Zhou M.-D, Wang H, Li L. Eur. J. Org. Chem. 2019; 2019: 3898
• 13g Gu X, Yuan H, Jiang J, Wu Y, Bai WJ. Org. Lett. 2018; 20: 7229
• 13h Shen R, Wang X, Zhang S, Dong C, Zhu D, Han L.-B. Adv. Synth. Catal. 2020; 362: 942
• 14 Wen L.-R, Sun Y.-X, Zhang J.-W, Guo W.-S, Li M. Green Chem. 2018; 20: 125
• 15a Wang L, Wu Y, Liu Y, Yang H, Liu X, Wang J, Li X, Jiang J. Org. Lett. 2017; 19: 782
• 15b Chen Z.-S, Zhou Z.-Z, Hua H.-L, Duan X.-H, Luo J.-Y, Wang J, Zhou P.-X, Liang Y.-M. Tetrahedron 2013; 69: 1065
• 15c Wu L, Zhang X, Chen QQ, Zhou AK. Org. Biomol. Chem. 2012; 10: 7859
• 15d Jiang H, Jin H, Abdukader A, Lin A, Cheng Y, Zhu C. Org. Biomol. Chem. 2013; 11: 3612
• 15e Hong G, Zhu X, Hu C, Aruma AN, Wu S, Wang L. J. Org. Chem. 2016; 81: 6867
• 16a Qian Y, Dai Q, Li Z, Liu Y, Zhang J. Org. Lett. 2020; 22: 4742
• 16b Kumara Swamy K, Uravakilli A, Kotikalapudi R. Synthesis 2014; 46: 1197
• 16c Pan J, Zhao R, Guo J, Ma D, Xia Y, Gao Y, Xu P, Zhao Y. Green Chem. 2019; 21: 792
• 16d Zhao Y, Chen T, Han D, Zhao C.-Q, Han L.-B. Org. Lett. 2014; 16: 6152
• 16e Zhang D, Lian M, Liu J, Tang S, Liu G, Ma C, Meng Q, Peng H, Zhu D. Org. Lett. 2019; 21: 2597
• 17a Gusarova NK, Volkov PA, Ivanova NI, Arbuzova SN, Khrapova KO, Albanov AI, Smirnov VI, Borodina TN, Trofimov BA. Tetrahedron Lett. 2015; 56: 4804
• 17b Trofimov BA, Volkov PA, Khrapova KO, Telezhkin AA, Ivanova NI, Albanov AI, Gusarova NK, Chupakhin ON. Chem. Commun. 2018; 54: 3371
• 17c Gusarova NK, Volkov PA, Ivanova NI, Khrapova KO, Albanov AI, Afonin AV, Borodina TN, Trofimov BA. Tetrahedron Lett. 2016; 57: 3776
• 17d Trofimov BA, Volkov PA, Khrapova KO, Telezhkin AA, Ivanova NI, Albanov AI, Gusarova NK, Belogolova AM, Trofimov AB. J. Org. Chem. 2019; 84: 6244
• 18a Liu C, Wei W, Yang D, Zheng Y, Bi Y, Chen M, Wang H. Tetrahedron 2015; 71: 6901
• 18b Fu Q, Yi D, Zhang Z, Liang W, Chen S, Yang L, Zhang Q, Ji J, Wei W. Org. Chem. Front. 2017; 4: 1385
• 18c Zhang Z.-J, Yi D, Fu Q, Liang W, Chen S.-Y, Yang L, Du F.-T, Ji J.-X, Wei W. Tetrahedron Lett. 2017; 58: 2417
• 18d Liang W, Zhang Z, Yi D, Fu Q, Chen S, Yang L, Du F, Ji J, Wei W. Chin. J. Chem. 2017; 35: 1378
• 18e Ke J, Tang Y, Yi H, Li Y, Cheng Y, Liu C, Lei A. Angew. Chem. Int. Ed. 2015; 54: 6604
• 19a Xie J, Li H, Xue Q, Cheng Y, Zhu C. Adv. Synth. Catal. 2012; 354: 1646
• 19b Xue Q, Xie J, Jin H, Cheng Y, Zhu C. Org. Biomol. Chem. 2013; 11: 1606
• 19c Huo C, Wang C, Wu M, Jia X, Wang X, Yuan Y, Xie H. Org. Biomol. Chem. 2014; 12: 3123
• 19d Yoo W.-J, Kobayashi S. Green Chem. 2014; 16: 2438
• 19e Lin B, Shi S, Lin R, Cui Y, Fang M, Tang G, Zhao Y. J. Org. Chem. 2018; 83: 6754
• 19f Tang G, Lin B, Lu G, Lin R, Cui Y, Liu Y, Zhao Y. Synlett 2018; 29: 2697
• 19g Wang J, Li J, Wei Y, Yang J, Huo C. Org. Chem. Front. 2018; 5: 3534
• 19h Huang Q, Dong K, Bai W, Yi D, Ji JX, Wei W. Org. Lett. 2019; 21: 3332
• 19i Gao Y, Huang Z, Zhuang R, Xu J, Zhang P, Tang G, Zhao Y. Org. Lett. 2013; 15: 4214
• 20a Zhang L, Liu W, Zhao X. Eur. J. Org. Chem. 2014; 2014: 6846
• 20b Makida Y, Usui K, Ueno S, Kuwano R. Chem. Lett. 2017; 46: 1814
• 20c Mao L.-L, Li C.-C, Yang Q, Cheng M.-X, Yang S.-D. Chem. Commun. 2017; 53: 4473
• 20d Wo X, Xie P, Fu W, Gao C, Liu Y, Sun Z, Loh T.-P. Chem. Commun. 2018; 54: 11132
• 21a Hu G, Shan C, Chen W, Xu P, Gao Y, Zhao Y. Org. Lett. 2016; 18: 6066
• 21b Mao L.-L, Li Y.-H, Yang S.-D. Org. Chem. Front. 2017; 4: 608
• 21c Shen R, Luo B, Yang J, Zhang L, Han L.-B. Chem. Commun. 2016; 52: 6451
• 21d Li X.-S, Han Y.-P, Zhu X.-Y, Li M, Wei W.-X, Liang Y.-M. J. Org. Chem. 2017; 82: 11636
• 21e Chen F, Xia Y, Lin R, Gao Y, Xu P, Zhao Y. Org. Lett. 2019; 21: 579
• 21f Song X.-R, Li R, Yang T, Bai J, Yang R, Chen X, Ding H, Xiao Q, Liang Y.-M. Tetrahedron Lett. 2018; 59: 3763
• 21g Li R, Chen X, Song X.-R, Ding H, Wang P, Xiao Q, Liang Y.-M. Adv. Synth. Catal. 2017; 359: 3962
• 21h Yang J, Zhang M, Qiu K, Wang L, Yu J, Xia Z, Shen R, Han L.-B. Adv. Synth. Catal. 2017; 359: 4417
• 21i Qian H, Huang D, Bi Y, Yan G. Adv. Synth. Catal. 2019; 361: 3240
• 22a Chen L, Fang X.-Y, Zou Y.-X. Org. Biomol. Chem. 2018; 16: 951
• 22b Chen L, Zou YX, Fang XY, Wu J, Sun XH. Org. Biomol. Chem. 2018; 16: 7417
• 22c Hu C, Hong G, He Y, Zhou C, Kozlowski MC, Wang L. J. Org. Chem. 2018; 83: 4739
• 23 Chen CC, Waser J. Chem. Commun. 2014; 50: 12923
• 24 Feng C.-G, Ye M, Xiao K.-J, Li S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 9322
• 25 Zhang H, Lin W, Wu Z, Ruan W, Wen T. Chem. Commun. 2015; 51: 3450
• 26 Si E, Zhao P, Wang L, Duan Z, Mathey F. Eur. J. Org. Chem. 2020; 2020: 697
• 27a Bai Y, Liu N, Wang S, Wang S, Ning S, Shi L, Cui L, Zhang Z, Xiang J. Org. Lett. 2019; 21: 6835
• 27b Dai Q, Li W, Li Z, Zhang J. J. Am. Chem. Soc. 2019; 141: 20556
• 27c Chrzanowski J, Krasowska D, Urbaniak M, Sieroń L, Pokora-Sobczak P, Demchuk OM, Drabowicz J. Eur. J. Org. Chem. 2018; 2018: 4614
• 27d Bloomfield J, Herzon S. Org. Lett. 2012; 14: 4370
• 27e Zhang HY, Sun M, Ma YN, Tian QP, Yang SD. Org. Biomol. Chem. 2012; 10: 9627
• 27f Keglevich G, Jablonkai E, Balázs LB. RSC Adv. 2014; 4: 22808
• 27g Berger O, Petit C, Deal EL, Montchamp J.-L. Adv. Synth. Catal. 2013; 355: 1361
• 27h Jablonkai E, Balázs LB, Keglevich G. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190: 660
• 27i Zhang X, Liu H, Hu X, Tang G, Zhu J, Zhao Y. Org. Lett. 2011; 13: 3478
• 27j Zeng H, Dou Q, Li CJ. Org. Lett. 2019; 21: 1301
• 27k Yuan J, To WP, Zhang ZY, Yue CD, Meng S, Chen J, Liu Y, Yu GA, Che CM. Org. Lett. 2018; 20: 7816
• 27l Xuan J, Zeng TT, Chen JR, Lu LQ, Xiao WJ. Chem. Eur. J. 2015; 21: 4962
• 27m Xu K, Yang F, Zhang G, Wu Y. Green Chem. 2013; 15: 1055
• 27n Zhao YL, Wu GJ, Li Y, Gao LX, Han FS. Chem. Eur. J. 2012; 18: 9622
• 28a Trost BM, Spohr SM, Rolka AB, Kalnmals CA. J. Am. Chem. Soc. 2019; 141: 14098
• 28b Ghosh T, Maity P, Kundu D, Ranu BC. New J. Chem. 2016; 40: 9556
• 28c Zhang J.-Q, Han L.-B. Org. Lett. 2020; 22: 4633
• 29a Chen L, Zhu Y, Chen T, Liu L, Zhang J.-S, Han L.-B. Org. Biomol. Chem. 2018; 16: 5090
• 29b Zhang JS, Chen T, Zhou Y, Yin SF, Han LB. Org. Lett. 2018; 20: 6746
• 30 Kurosawa MB, Isshiki R, Muto K, Yamaguchi J. J. Am. Chem. Soc. 2020; 142: 7386
• 31a Wang M, Yang J, Wang S, Zhong H. Tetrahedron Lett. 2020; 61: 151971
• 31b Liao LL, Gui YY, Zhang XB, Shen G, Liu HD, Zhou WJ, Li J, Yu DG. Org. Lett. 2017; 19: 3735
• 31c Yang J, Xiao J, Chen T, Han LB. J. Org. Chem. 2016; 81: 3911
• 31d Yang J, Chen T, Han LB. J. Am. Chem. Soc. 2015; 137: 1782
• 31e Luo H, Liu H, Chen X, Wang K, Luo X, Wang K. Chem. Commun. 2017; 53: 956
• 31f Zhang J.-S, Chen T, Han L.-B. Eur. J. Org. Chem. 2020; 2020: 1148
• 31g Isshiki R, Muto K, Yamaguchi J. Org. Lett. 2018; 20: 1150
• 31h Fu T, Qiao H, Peng Z, Hu G, Wu X, Gao Y, Zhao Y. Org. Biomol. Chem. 2014; 12: 2895
• 31i Dong J, Liu L, Ji X, Shang Q, Liu L, Su L, Chen B, Kan R, Zhou Y, Yin SF, Han LB. Org. Lett. 2019; 21: 3198
• 31j Zhang JS, Chen T, Yang J, Han LB. Chem. Commun. 2015; 51: 7540
• 31k Sun M, Zhang HY, Han Q, Yang K, Yang SD. Chem. Eur. J. 2011; 17: 9566
• 31l Yang J, Xiao J, Chen T, Yin S.-F, Han L.-B. Chem. Commun. 2016; 52: 12233
• 32 Liu L, Lv Y, Wu Y, Gao X, Zeng Z, Gao Y, Tang G, Zhao Y. RSC Adv. 2014; 4: 2322
• 33a Xia M, Cheng J. Tetrahedron Lett. 2016; 57: 4702
• 33b Crocker RD, Hussein MA, Ho J, Nguyen TV. Chem. Eur. J. 2017; 23: 6259
• 33c Yan Z, Lin S, Min C, Zhang R, Liu Q. Synlett 2018; 29: 2027
• 33d He W, Wang Z, Li X, Yu Q, Wang Z. Tetrahedron 2016; 72: 7594
• 33e Wang D, Zhao J, Xu W, Shao C, Shi Z, Li L, Zhang X. Org. Biomol. Chem. 2017; 15: 545
• 33f Kumaraswamy G, Raju R. Adv. Synth. Catal. 2014; 356: 2591
• 33g Zhang X, Shi Z, Shao C, Zhao J, Wang D, Zhang G, Li L. Eur. J. Org. Chem. 2017; 2017: 1884
• 33h Gong X, Chen J, Liu J, Wu J. Org. Chem. Front. 2017; 4: 2221
• 33i Zhang L, Zhang P, Li X, Xu J, Tang G, Zhao Y. J. Org. Chem. 2016; 81: 5588
• 33j Zhang X, Mei Y, Li Y, Hu J, Huang D, Bi Y. Asian J. Org. Chem. 2021; 10: 453
• 34a Handoko, Benslimane Z, Arora PS. Org. Lett. 2020; 22: 5811
• 34b Li R, Shi T, Chen X.-L, Lv Q.-Y, Zhang Y.-L, Peng Y.-Y, Qu L.-B, Yu B. New J. Chem. 2019; 43: 13642
• 35a Volkov PA, Petrushenko KB, Ivanova NI, Khrapova KO, Larina LI, Gusarova NK, Trofimov BA. Tetrahedron Lett. 2017; 58: 1992
• 35b Anitha T, Ashalu KC, Sandeep M, Mohd A, Wencel-Delord J, Colobert F, Reddy KR. Eur. J. Org. Chem. 2019; 2019: 7463
• 36a Deng L, Wang Y, Mei H, Pan Y, Han J. J. Org. Chem. 2019; 84: 949
• 36b Li QY, Swaroop TR, Hou C, Wang ZQ, Pan YM, Tang HT. Adv. Synth. Catal. 2019; 361: 1761
• 36c Yu X, Zhang S, Jiang Z, Zhang H.-S, Wang T. Eur. J. Org. Chem. 2020; 2020: 3110
• 36d Ou Y, Huang Y, He Z, Yu G, Huo Y, Li X, Gao Y, Chen Q. Chem. Commun. 2020; 56: 1357
• 37a He W, Hou X, Li X, Song L, Yu Q, Wang Z. Tetrahedron 2017; 73: 3133
• 37b Sun JG, Yang H, Li P, Zhang B. Org. Lett. 2016; 18: 5114
• 37c Song S, Zhang Y, Yeerlan A, Zhu B, Liu J, Jiao N. Angew. Chem. Int. Ed. 2017; 56: 2487
• 37d Xue J.-W, Zeng M, Zhang S, Chen Z, Yin G. J. Org. Chem. 2019; 84: 4179
• 37e Li Y, Yang Q, Yang L, Lei N, Zheng K. Chem. Commun. 2019; 55: 4981
• 37f Li S, Chen T, Saga Y, Han L.-B. RSC Adv. 2015; 5: 71544
• 38 Liu N, Mao LL, Yang B, Yang SD. Chem. Commun. 2014; 50: 10879