Synlett 2020; 31(01): 21-34
DOI: 10.1055/s-0039-1691496
account
© Georg Thieme Verlag Stuttgart · New York

Organosilicon-Mediated Organic Synthesis (SiMOS): A Personal Account

Li Li
a  Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou 311121, P. R. of China
b  College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China   Email: liwenxu@hznu.edu.cn
,
Yun-Long Wei
a  Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Li-Wen Xu
a  Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou 311121, P. R. of China
b  College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China   Email: liwenxu@hznu.edu.cn
› Author Affiliations
We thank National Natural Science Foundation of China (Grant No. 21703051, 21773051, 21801056) and Natural Science Foundation of Zhejiang Province (Grant No. LZ18B020001, LY17B030005, LY17E030003, and LQ19B040001) for financial support of this work.
Further Information

Publication History

Received: 04 October 2019

Accepted after revision: 20 October 2019

Publication Date:
11 November 2019 (online)


Abstract

The organosilicon-mediated organic synthesis (SiMOS) has attracted much attention over the recent decades. However, the use of organosilicon reagents with novel catalytic strategies remains to be explored. This Account summarizes our group’s progress mainly based on the application of a wide variety of organosilicon reagents, including allylic silanes, trifluoromethyl silane, acylsilanes, chlorosilanes, hydrosilanes, trimethylsilyldiazomethane, trimethylsiloxyfuran, silanols, α-trimethylsilylmethylacetate, and trimethylsilylcyanide, in catalysis and organic reactions. These transformations were proved to be alternative procedures for the construction of structurally diverse compounds.

1 Introduction

2 The Exploration of New Reactivity of Organosilicon Reagent in Organic Synthesis

2.1 Allylic Silanes

2.2 Trifluomethylsilane (TMSCF3)

2.3 Acylsilanes

2.4 Chlorosilanes and Hydrosilanes

2.5 Trimethylsilyldiazomethane (TMSD)

2.6 Trimethylsiloxyfuran

2.7 Silanols

2.8 Trimethylsilylcyanide (TMSCN)

3 Conclusion and Perspective

 
  • References


    • For recent reviews, see:
    • 1a Huang HT, Li T, Wang JZ, Qin GP, Xiao TB. Chin. J. Org. Chem. 2019; 39: 1511
    • 1b Tsurugi H, Mashima K. Acc. Chem. Res. 2019; 52: 769
    • 1c Wang DX, Cao JF, Hang DD, Li WS, Feng SY. Prog. Chem. 2019; 31: 110
    • 1d Muthukumaran N, Velappan K, Gour K, Prabusankar G. Coord. Chem. Rev. 2018; 377: 1
    • 1e Hailes RL. N, Oliver AM, Gwyther J, Whittell GR, Manners I. Chem. Soc. Rev. 2016; 45: 5358

      For recent reviews, see:
    • 2a Chi H, Wang MY, Xiao YT, Wang FK, Joshy KS. Molecules 2018; 23: 2481
    • 2b Tsunoyama H, Shibuta M, Nakaya M, Eguchi T, Nakajima A. Acc. Chem. Res. 2018; 51: 1735
    • 2c Zhang LY, Yao WH, Gao YZ, Zhang CH, Yang H. Polymers 2017; 10: 794
    • 2d Vlasova NN, Sorokin MS, Oborina EN. Appl. Organomet. Chem. 2017; 31: e3668
    • 2e Wang D, Klein J, Mejia E. Chem. Asian J. 2017; 12: 1180
    • 2f Remond E, Martin C, Martinez J, Cavelier F. Chem. Rev. 2016; 116: 11654
    • 3a Zhao ZJ, Guo YJ, Tao J, Chang ZF, Lam JW. Y, Xu LW, Qiu HY, Tan BZ. Macromol. Rapid Commun. 2012; 33: 1074
    • 3b Zhao ZJ, Jiang T, Guo YJ, Ding LY, He BR, Chang ZF, Lam JW. Y, Liu JZ, Chan CY. K, Lu P, Xu LW, Qiu HY, Tan BZ. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 2265
    • 3c Li WD, Han SH, Lui YH, Chen JX. Chin. J. Org. Chem. 2017; 9: 2423
    • 3d Yang Q, Liu L, Zhang WX, Xi ZF. Chin. J. Org. Chem. 2018; 38: 272
    • 4a Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631
    • 4b Indukuri K, Cornelissen L, Riant O. Synthesis 2016; 48: 4400
  • 5 Paquette LA. Science 1982; 217: 793
  • 6 Xu LW. Chiral Organosilicon Compounds. In Organosilicon Compounds: Theory and Experiment (Synthesis). Lee VY. Academic Press; London: 2017: 145
  • 7 Allred AL, Rochow EG. J. Inorg. Nucl. Chem. 1958; 5: 264
  • 8 Brook MA. Silicon in Organic, Organometallic, and Polymer Chemistry. Wiley-Interscience; New York: 1999
  • 9 Reagents for Silicon-Mediated Organic Synthesis . Philip LF. John Wiley and Sons; New York: 2011
    • 10a Rappoport Z, Apeloig Y. The Chemistry of Organic Silicon Compounds . John Wiley and Sons; New York: 1998
    • 10b Yang MS, Xu LW, Qiu HY, Lai GQ, Jiang JX. Tetrahedron Lett. 2008; 49: 253
    • 10c Xu LW, Ju YD, Li L, Qiu HY, Jiang JX, Lai GQ. Tetrahedron Lett. 2008; 49: 7037
    • 10d Simon MO, Martinez R, Genêt JP, Darse S. Adv. Synth. Catal. 2009; 351: 153
    • 10e Sakamoto S, Shimojima A, Miyasaka K, Ruan J, Terasaki O, Kuroda K. J. Am. Chem. Soc. 2009; 131: 9634
    • 10f Tan G, Yang Y, Chu C, Zhu H, Roesky HW. J. Am. Chem. Soc. 2010; 132: 12231
    • 10g Shoji Y, Higashihara T, Watanabe J, Ueda M. Marcromolecules 2010; 43: 805
    • 10h Missaghi MN, Galloway JM, Kung HH. Organometallics 2010; 29: 3769
    • 11a Beckmann J, Duthie A, Reeske G, Schürmann M. Organometallics 2005; 24: 3629
    • 11b Liang JL, Barnes K, Akdag A, Worley SD, Worley D, Lee J, Broughton RM, Huang TS. Ind. Eng. Chem. Res. 2007; 46: 1861
    • 11c Thompson DB, Brook MA. J. Am. Chem. Soc. 2008; 130: 32

      Representative reviews:
    • 12a Fleming I, Barbero A, Walter D. Chem. Rev. 1997; 97: 2063
    • 12b Horn KA. Chem. Rev. 1995; 95: 1317
    • 12c Prakash GK, Yudin AK. Chem. Rev. 1997; 97: 757
    • 12d Paquette LA. Chem. Rev. 1986; 86: 73
    • 12e Masse CE, Panek JS. Chem. Rev. 1995; 95: 1293
    • 12f Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375
    • 13a Sahoo B, Brandstadt KF, Lane TH, Gross RA. Org. Lett. 2005; 7: 3857
    • 13b Naga N, Kihara Y, Miyanaga T, Furukawa H. Marcromolecules 2009; 42: 3454

      Selected examples:
    • 14a Franz AK, Woerpel KA. Acc. Chem. Res. 2000; 33: 813
    • 14b Dilman AD, Ioffe SL. Chem. Rev. 2003; 103: 733
    • 14c Naka H, Koseki D, Kondo Y. Adv. Synth. Catal. 2008; 350: 1901
    • 14d Xu LW, Li L, Shi ZH. Adv. Synth. Catal. 2010; 352: 243
    • 14e Leighton JL. Aldrichimica Acta 2010; 43: 3

    • Oxidation:
    • 14f Mader MM, Norrby PO. J. Am. Chem. Soc. 2001; 123: 1970
    • 14g Tamao K, Kakui T, Kumada M. J. Am. Chem. Soc. 1978; 100: 2268
    • 14h Spletstoser JT, Zacuto PJ, Leighton JL. Org. Lett. 2008; 10: 5593
    • 14i Fleming I, Henning R, Plaut H. J. Chem. Soc., Chem. Commun. 1984; 29

    • Cross-coupling:
    • 14j Denmark SE, Pan W. Org. Lett. 2001; 3: 61
    • 14k Denmark SE, Sweis RF. Acc. Chem. Res. 2002; 35: 835
    • 14l Handy CJ, Manoso AS, McElroy WT, Seganish WM, DeShong P. Tetrahedron 2005; 61: 12201
    • 14m Seganish WM, DeShong P. Org. Lett. 2006; 8: 3951
    • 14n Denmark SE, Smith RC, Chang WT. T, Muhuhi JM. J. Am. Chem. Soc. 2009; 131: 3104
    • 14o Denmark SE, Liu JH. C. Angew. Chem. Int. Ed. 2010; 49: 2978

    • Cycloaddition:
    • 14p Tran K, Leighton JL. Adv. Synth. Catal. 2006; 348: 16
    • 14q Halvorsen GT. W, Roush R. Org. Lett. 2007; 9: 2243
    • 14r Baxter RD, Montgomery J. J. Am. Chem. Soc. 2008; 130: 9662
    • 15a Chemler SR, Roush WR. Modern Carbonyl Chemistry. Otera J. Wiley-VCH; New York: 2000. Chap. 11, 403
    • 15b Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207
  • 16 Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
    • 17a Li CJ, Zhang WC. J. Am. Chem. Soc. 1998; 120: 9102
    • 17b Watahiki T, Oriyama T. Tetrahedron Lett. 2002; 43: 8959
    • 17c Sinha P, Roy S. Organometallics 2004; 23: 67
    • 17d Tang L, Ding L, Chang WX, Li J. Tetrahedron Lett. 2006; 47: 303
  • 18 Gomes P, Gosmini C, Périchon J. Synthesis 2003; 1909
  • 19 Shi SL, Xu LW, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 6638
    • 20a Yanagisawa A, Nakamura Y, Arai T. Tetrahedron: Asymmetry 2004; 15: 1909
    • 20b Solin N, Kjellgren JK, Szabó J. J. Am. Chem. Soc. 2004; 126: 7026
    • 20c Kadota I, Yamamoto Y. Acc. Res. Chem. 2005; 38: 423
    • 21a Hollis TK, Bosnich B. J. Am. Chem. Soc. 1995; 117: 4570
    • 21b Bottoni A, Costa AL, Tommaso DD, Rossi I, Tagliavini E. J. Am. Chem. Soc. 1997; 119: 12131
    • 21c Denmark SE, Su XP, Nishigaichi Y, Coe DM, Wong KT, Winter SB. D, Choi JY. J. Org. Chem. 1999; 64: 1958
    • 21d Yamasaki S, Fujii K, Wada R, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2002; 124: 6536
    • 21e Kinnaird JW. A, Ng PY, Kubota K, Wang X, Leighton J. J. Am. Chem. Soc. 2002; 124: 7920
    • 21f Ogawa C, Sugiura M, Kobayashi S. Chem. Commun. 2003; 676
    • 21g Wadamoto M, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 14556
    • 21h Williams DR, Morales-Ramos AI, Williams CM. Org. Lett. 2006; 8: 4393 ; and references cited therein
    • 21i Jagtap SB, Tsogoeva SB. Chem. Commun. 2006; 4747
    • 22a Yang Y, Wang M, Wang D. Chem. Commun. 1997; 1654
    • 22b Wang Z, Kisanga P, Verkade J. J. Org. Chem. 1999; 64: 6459
    • 22c Rowlands GJ, Barnes WK. Chem. Commun. 2003; 2712
    • 22d Evans DA, Aye Y, Wu J. Org. Lett. 2006; 8: 2071
    • 23a Nosse B, Chhor RB, Jeong WB, Böhm C, Reiser O. Org. Lett. 2003; 5: 941
    • 23b Pospíšil J, Kumamoto T, Markó I. Angew. Chem. Int. Ed. 2006; 45: 3357
    • 24a Aoyama N, Hamada T, Manabe K, Kobayashi S. J. Org. Chem. 2003; 68: 7329
    • 24b Wieland LC, Zerth HM, Mohan RS. Tetrahedron Lett. 2002; 43: 4597
    • 24c Wadamoto M, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 14556
    • 24d Jung ME, Maderna A. Tetrahedron Lett. 2004; 45: 5301
  • 25 Yang MS, Xu LW, Zhang FB, Qiu HY, Jiang JX, Lai GQ. Appl. Organomet. Chem. 2008; 22: 177
  • 26 Yang MS, Xu LW, Qiu HY, Lai GQ, Jiang JX. Tetrahedron Lett. 2008; 49: 253
    • 27a Mekhalfia A, Markó IE. Tetrahedron Lett. 1991; 32: 4779
    • 27b Watahiki T, Akabane Y, Oriyama T. Org. Lett. 2003; 5: 3045
    • 27c Anzalone PW, Mohan RS. Synthesis 2005; 2661
  • 28 Du Y, Xu LW, Shimizu Y, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 16146
    • 29a Greene TW, Wuts PG. M. In Protective Groups in Organic Synthesis, 3rd ed. Wiley-Interscience; New York: 1999. Chap. 2
    • 29b Stolarzewicz A, Grobelny Z, Pisarski W, Losiewicz B, Peikarnik B, Swinarew A. Eur. J. Org. Chem. 2006; 2485
    • 29c Corma A, Renz M. Angew. Chem. Int. Ed. 2007; 46: 298
    • 30a Colvin E. Silicon in Organic Synthesis. Butterworth; London: 1981: 97
    • 30b Weber WP. Silicon Reagents for Organic Synthesis. Vol. 12. Springer; Berlin: 1983: 173
    • 30c Majetich G, Behnke M, Hull K. J. Org. Chem. 1985; 50: 3615
    • 30d Hosomi A. Acc. Chem. Res. 1988; 21: 200
    • 30e Fleming I, Dunogues J, Smithers R. Org. React. 1989; 37: 57
    • 30f Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375
    • 30g Tori M, Makino C, Hisazumi K, Sono M, Nakashima K. Tetrahedron: Asymmetry 2001; 12: 301
    • 31a Schinzer D. Angew. Chem., Int. Ed. Engl. 1984; 23: 308
    • 31b Kuhnert N, Peverley J, Robertson J. Tetrahedron Lett. 1998; 39: 3215
    • 31c Lee PH, Lee K, Sung SY, Chang S. J. Org. Chem. 2001; 66: 8646
    • 31d Yadav JS, Reddy BV. S, Sadasiv K, Satheesh G. Tetrahedron Lett. 2002; 43: 9695
    • 31e Lee PH, Seomoon D, Kim S, Nagaiah K, Damle SV, Lee K. Synthesis 2003; 2189
    • 31f Stevens BD, Nelson SG. J. Org. Chem. 2005; 70: 4375
    • 32a Zhou W, Li L, Xu LW, Qiu HY, Lai GQ, Xia CG. Synth. Commun. 2008; 38: 1638
    • 32b Gao YH, Yang L, Zhou W, Xu LW, Xia CG. Appl. Organomet. Chem. 2009; 23: 114
    • 32c Jiang ZY, Wu JR, Li L, Chen XH, Lai GQ, Jiang JX. Cent. Eur. J. Chem. 2010; 8: 669
    • 32d Jiang ZY, Zhang CH, Gu FL, Yang KF, Lai GQ, Xu LW. Synlett 2010; 1251
    • 32e Yang HM, Gao YH, Li L, Jiang ZY, Lai GQ, Xia CG, Xu LW. Tetrahedron Lett. 2010; 51: 3836
  • 33 Xu LW, Yang MS, Qiu HY, Lai GQ, Jiang JX. Synth. Commun. 2008; 38: 1011
    • 34a Nie J, Guo HC, Cahard D, Ma JA. Chem. Rev. 2011; 111: 455
    • 34b Dolfen J, de Kimpe N, Dhooghe M. Synlett 2016; 27: 1486
    • 34c Ma JA, Cahard D. Chem. Rev. 2004; 104: 6119
    • 34d Caron S, Do NM, Sieser JE, Arpin P, Vazquez E. Org. Process Res. Dev. 2007; 11: 1015
    • 34e Boechat N, Bastos MM. Curr. Org. Chem. 2010; 7: 403
    • 35a Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
    • 35b Zhang C. Adv. Synth. Catal. 2017; 365: 372
  • 36 Dong C, Bai XF, Lv JY, Cui YM, Cao J, Zheng ZJ, Xu LW. Molecules 2017; 22: 769

    • Reviews:
    • 37a Ricci A, Degl’Innocenti A. Synthesis 1986; 647
    • 37b Jurczak J, Golebiowski A. Chem. Rev. 1989; 89: 149
    • 37c Page PC. B, Klair SS, Rosenthal S. Chem. Soc. Rev. 1990; 19: 147

    • For our work on copper-catalyzed conjugate addition of diethylzinc to α,β-unsaturated acylsilanes, see:
    • 37d Ye F, Zheng ZJ, Deng WH, Zheng LS, Deng Y, Xia CG, Xu LW. Chem. Asian J. 2013; 8: 2242
    • 37e Lv JY, Zheng ZJ, Li L, Cui YM, Xu Z, Cao J, Yang KF, Xu LW. RSC Adv. 2017; 7: 54934
    • 38a Corey EJ, Luo G, Lin LS. Angew. Chem. Int. Ed. 1998; 37: 1126
    • 38b Berber H, Brigaud T, Lefebvre O, Plantier-Royon R, Portella C. Chem. Eur. J. 2001; 7: 903
    • 38c Nicewicz DA, Satterfirld AD, Schmit DC, Johnson JS. J. Am. Chem. Soc. 2008; 130: 17281
    • 38d Behenna DC, Corey EJ. J. Am. Chem. Soc. 2008; 130: 6720
    • 38e Lettan RB. II, Woodward CC, Scheidt KA. Angew. Chem. Int. Ed. 2008; 47: 2294
  • 39 Zhang HJ, Pribbenow DL, Bolm C. Chem. Soc. Rev 2013; 42: 8540
    • 40a Paredes MD, Alonso R. J. Org. Chem. 2000; 65: 2292
    • 40b Nicewicz DA, Yates CM, Johnson JS. J. Org. Chem. 2004; 69: 6548
  • 41 Honda M, Ohkura N, Saisyo S.-I, Segi M, Nakajima T. Tetrahedron 2003; 59: 8203
  • 42 Bai XF, Gao G, Zheng ZJ, Li F, Lai GQ, Jiang K, Li F, Xu LW. Synlett 2011; 3031
    • 43a Takeda K, Ohnishi Y, Koizumi T. Org. Lett. 1999; 1: 237
    • 43b Arai N, Suzuki K, Sugizaki S, Sorimachi H, Ohkuma T. Angew. Chem. Int. Ed. 2008; 47: 1770
  • 44 Gao G, Bai XF, Li F, Zheng LS, Zheng ZJ, Lai GQ, Jiang K, Li F, Xu LW. Tetrahedron Lett. 2012; 53: 2164
    • 45a Shen H, Lu X, Jiang KZ, Yang KF, Lu Y, Zheng ZJ, Lai GQ, Xu LW. Tetrahedron Lett. 2012; 68: 8916
    • 45b Bai XF, Deng WH, Xu Z, Li FW, Deng Y, Xia CG, Xu LW. Chem. Asian J. 2014; 9: 1108
  • 46 Xu LW, Li L, Xia CG, Zhao PQ. Tetrahedron Lett. 2004; 45: 2435
    • 47a Xu LW, Wang ZT, Xia CG, Li L, Zhao PQ. Helv. Chim. Acta. 2004; 87: 2608
    • 47b Xu LW, Xia CG. Synthesis 2004; 2191
    • 47c Xu LW, Xia CG. Tetrahedron Lett. 2004; 45: 4507
    • 47d Xu LW, Xia CG, Li L. J. Org. Chem. 2004; 69: 8482
    • 47e Xu LW, Xia CG, Hu XX. Chem. Commun. 2003; 2570
    • 47f Yang L, Xu LW, Xia CG. Tetrahedron Lett. 2007; 48: 1599
    • 47g Xu LW, Zhou W, Yang L, Xia CG. Synth. Commun. 2007; 38: 3095
    • 47h Deng WH, Ye F, Bai XF, Li L, Song T, Wei YL, Xu LW. RSC Adv. 2014; 4: 479
    • 48a Yang HM, Li L, Li F, Jiang KZ, Shang JY, Lai GQ, Xu LW. Org. Lett. 2011; 13: 6508
    • 48b Cai YF, Li L, Luo MX, Yang KF, Lai GQ, Jiang JX, Xu LW. Chirality 2011; 23: 397
  • 49 Xu LW, Chen XH, Shen H, Deng Y, Jiang JX, Jiang K, Lai GQ, Sheng CQ. Eur. J. Org. Chem. 2012; 290
    • 50a Peterson DJ. J. Org. Chem. 1968; 33: 780
    • 50b Ager DJ. Org. React. 1990; 38: 1
    • 50c Assadi N, Pogodin S, Agranat I. Eur. J. Org. Chem. 2011; 6773
    • 50d Wei GQ, Cohen T. Synlett 2011; 2697
    • 50e McNulty J, Das P, Gosciniak D. Tetrahedron Lett. 2008; 49: 281
    • 50f Fernandez MC, Diaz A, Guillin JJ, Blanco O, Ruiz M, Ojea V. J. Org. Chem. 2006; 71: 6958
    • 50g Pulido FJ, Barberdo A. Nat. Protoc. 2006; 1: 2068
    • 51a Robert P, Roman R. J. Organomet. Chem. 1988; 341: 549
    • 51b Yu J, Spencer JB. J. Am. Chem. Soc. 1997; 119: 5257
    • 51c Yu J, Gaunt M, Spencer JB. J. Org. Chem. 2002; 67: 4627
    • 51d Dunne JO, Duckett SB, Konya D, Leñero KQ, Drent E. J. Am. Chem. Soc. 2004; 126: 16708
    • 51e Kluwer AM, Koblenz TS, Jonischkeit T, Woelk K, Elesevier C. J. Am. Chem. Soc. 2005; 127: 15470
    • 51f Kim IS, Dong GR, Jung YH. J. Org. Chem. 2007; 72: 5424
    • 51g Brandt B, Fischer J.-H, Ludwig W, Libuda J, Zaera F, Schauermann S, Freund H.-J. J. Phys. Chem. C 2008; 112: 11408
  • 52 Bai XF, Xu LW, Zheng LS, Jiang JX, Lai GQ, Shang JY. Chem. Eur. J. 2012; 18: 8174
    • 53a Wang H, Li L, Bai XF, Shang JY, Yang KF, Xu LW. Adv. Synth. Catal. 2013; 355: 341
    • 53b Wang H, Li L, Bai XF, Deng WH, Zheng ZJ, Yang KF, Xu LW. Green Chem. 2013; 15: 2349
    • 53c Wang H, Yang KF, Li L, Bai Y, Zheng ZJ, Zhang WQ, Gao Z, Xu LW. ChemCatChem 2014; 6: 580
    • 53d Wang H, Zhang J, Cui YM, Yang KF, Zheng ZJ, Xu LW. RSC Adv. 2014; 4: 34681
    • 53e Dong XY, Lin Y, Cui YM, Yang KF, Zheng ZJ, Xu LW. ChemistrySelect 2016; 1: 2400
    • 53f Li N, Dong XY, Zhang JL, Yang KF, Gao ZW, Zheng ZJ, Zhang WQ, Xu LW. RSC Adv. 2017; 7: 50729
    • 53g Long PW, Xu JX, Bai XF, Xu Z, Zheng ZJ, Yang KF, Li L, Xu LW. RSC Adv. 2018; 8: 22944
  • 54 Schramm Y, Barrios-Landeros F, Pfaltz A. Chem. Sci. 2013; 4: 2760
  • 55 Wang H, Yang KF, Li L, Bai Y, Zheng ZJ, Zhang WQ, Gao ZW, Xu LW. ChemCatChem 2014; 6: 580
  • 56 Bai XF, Song T, Deng WH, Wei YL, Li L, Xia CG, Xu LW. Synlett 2014; 25: 417
    • 57a Corey JY, Braddock-Wilking J. Chem. Rev. 1999; 99: 175
    • 57b Shang JY, Li F, Bai XF, Jiang JX, Yang KF, Lai GQ, Xu LW. Eur. J. Org. Chem. 2012; 2809
  • 58 Chen XH, Xu LW, Deng Y, Jiang KZ, Lai GQ, Ni Y, Yang KF, Jiang JX. Eur. J. Org. Chem. 2011; 1736

    • For recent reviews, see:
    • 59a Xia Y, Qiu D, Wang J. Chem. Rev. 2017; 117: 13810
    • 59b Xia Y, Wang J. Chem. Soc. Rev. 2017; 46: 2306
  • 60 Mu QC, Wang XB, Ye F, Sun YL, Bai XF, Chen J, Xia CG, Xu LW. Chem. Commun. 2018; 54: 12994
  • 61 Themed issue on Recent Advances in Organosilicon Chemistry directed towards Organic Synthesis: Langer, P. Ed.; Tetrahedron 2009, 65, 5445.
    • 62a Wieland LC, Vieira EM, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 570
    • 62b Mandai H, Mandai K, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 17961
  • 63 Casiraghi G, Battistini L, Curti C, Rassu G, Zanardi F. Chem. Rev. 2011; 111: 3076
    • 64a Xu Z, Xu LW. Chem. Rec. 2015; 15: 925
    • 64b Zheng LS, Li L, Yang KF, Zheng ZJ, Xiao XQ, Xu LW. Tetrahedron 2013; 69: 8777
  • 65 Krenske EH, Houk KN. Acc. Chem. Res. 2013; 46: 979
  • 66 Habata Y, Taniguchi A, Ikeda M, Hiraoka T, Matsuyama N, Otsuka S, Kuwahara S. Inorg. Chem. 2013; 52: 2542

    • For recent examples, see:
    • 67a Wang K, Zhou J, Jiang Y, Zhang M, Wang C, Xue D, Tang W, Sun H, Xiao J, Li C. Angew. Chem. Int. Ed. 2019; 58: 6380
    • 67b Roesch P, Meller R, Dallmann A, Scholz G, Kaupp M, Braun T, Braun-Cula B, Wittwer P. Chem. Eur. J. 2019; 25: 4678
    • 67c Koo J, Kim SH, Hong SH. Chem. Commun. 2018; 54: 4995
  • 68 Ye F, Zheng ZJ, Li L, Yang KF, Xia CG, Xu LW. Chem. Eur. J. 2013; 19: 15452
    • 69a Gavrilov KN, Zheglov SV, Rastorguev EA, Groshkin NN, Maksimova MG, Benetsky EB, Davankov VA, Reetz MT. Adv. Synth. Catal. 2010; 352: 2599
    • 69b Wu KH, Zhou S, Chen CA, Yang MC, Chiang RT, Chen CR, Gau HM. Chem. Commun. 2011; 47: 11668
    • 69c Wu KH, Gau HM. J. Am. Chem. Soc. 2006; 128: 14808
    • 69d Salvi L, Kim JG, Walsh PJ. J. Am. Chem. Soc. 2009; 131: 12483
  • 70 Li F, Zhou W, Zheng LS, Li L, Zheng ZJ, Xu LW. Synth. Commun. 2014; 44: 2861
    • 71a Li F, Zheng ZJ, Shang JY, Jiang KZ, Lai GQ, Jiang JX, Xu LW. Chem. Asian J. 2012; 7: 2008
    • 71b Wei YL, Yang KF, Li F, Zheng ZJ, Xu Z, Xu LW. RSC Adv. 2014; 4: 37859

      For recent reviews, see:
    • 72a North M, Usanov DL, Young C. Chem. Rev. 2009; 108: 5146
    • 72b Khan NH, Kureshy RI, Abdi SH. R, Agrawal S, Jasra RV. Coord. Chem. Rev. 2008; 252: 593

      For selected and recent examples, see:
    • 73a Zhang HD, Zou Y, Wang YM, Shen Y, Zheng XX. Chem. Eur. J. 2014; 20: 7830
    • 73b Liu W, Groves JT. Angew. Chem. Int. Ed. 2013; 52: 6024
  • 74 Wei YL, Huang WS, Cui YM, Yang KF, Xu Z, Xu LW. RSC Adv. 2015; 5: 3098
    • 75a Xu LW, Li L, Shi ZH. Adv. Synth. Catal. 2010; 352: 243
    • 75b Shen H, Yang KF, Shi ZH, Jiang JX, Lai GQ, Xu LW. Eur. J. Org. Chem. 2011; 5031
    • 75c Shi ZH, Sheng H, Yang KF, Jiang JX, Lai GQ, Lu Y, Xu LW. Eur. J. Org. Chem. 2011; 66
    • 75d Song T, Li L, Zhou W, Zheng ZJ, Deng Y, Xu Z, Xu LW. Chem. Eur. J. 2015; 21: 554
    • 75e Chen MY, Song T, Zheng ZJ, Xu Z, Cui YM, Xu LW. RSC Adv. 2016; 6: 58698
    • 75f Chen MY, Chen L, Xu Z, Song T, Zheng ZJ, Cao J, Cui YM, Xu LW. ChemCatChem 2018; 10: 280
    • 75g Yuan Y, Zheng ZJ, Li L, Bai XF, Xu Z, Cui YM, Cao J, Yang KF, Xu LW. Adv. Synth. Catal. 2018; 360: 3002
    • 75h Sun FN, Yang WC, Chen XB, Sun YL, Cao J, Xu Z, Xu LW. Chem. Sci. 2019; 10: 7579