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Synthesis 2022; 54(17): 3739-3752
DOI: 10.1055/a-1786-6496
DOI: 10.1055/a-1786-6496
feature
Visible-Light-Induced Catalysis: A Regioselectivity Switch between [2+1] and [2+2] Cycloaddition of Diazocarbonyls with Olefins
We thank the Taishan Scholars Construction Projects of Shandong (tsqn201812075), the Natural Science Foundation of Shandong Province for Distinguished Young Scholars (ZR2020JQ07), Youth Innovation Science and Technology Plan of Colleges and Universities in Shandong Province (2019KJC003), and Qingdao University of Science & Technology for financial support.
Abstract
Visible-light-promoted [2+1] and [2+2] cycloaddition reactions of diazocarbonyls with olefins have been developed, affording functionalized cyclopropanes and cyclobutanes, respectively. In visible-light catalysis of Ir(ppy)3, a simple addition of Rh2(OAc)4 switches the regioselectivity from [2+1] to [2+2] cycloaddition with good reactivity and high regioselectivity.
Key words
photocatalysis - Rh2(OAc)4 - cycloaddition - α-diazo compounds - switchable regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1786-6496.
- Supporting Information
Publikationsverlauf
Eingereicht: 02. März 2022
Angenommen nach Revision: 02. März 2022
Accepted Manuscript online:
02. März 2022
Artikel online veröffentlicht:
07. April 2022
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References
- 1a Doyle MP, Forbes DC. Chem. Rev. 1998; 98: 911
- 1b Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
- 1c Davies HM. L, Manning JR. Nature 2008; 451: 417
- 1d Zhao X, Zhang Y, Wang J. Chem. Commun. 2012; 48: 10162
- 1e Zhu S.-F, Zhou Q.-L. Acc. Chem. Res. 2012; 45: 1365
- 1f Davies HM. L, Lian Y. Acc. Chem. Res. 2012; 45: 923
- 1g Guo X, Hu W. Acc. Chem. Res. 2013; 46: 2427
- 1h Gillingham D, Fei N. Chem. Soc. Rev. 2013; 42: 4918
- 1i Ford A, Miel H, Ring A, Slattery CN, Maguire AR, McKervey MA. Chem. Rev. 2015; 115: 9981
- 1j Chanthamath S, Iwasa S. Acc. Chem. Res. 2016; 49: 2080
- 1k Cheng Q.-Q, Deng Y, Lankelma M, Doyle MP. Chem. Soc. Rev. 2017; 46: 5425
- 1l Shim SY, Ryu DH. Acc. Chem. Res. 2019; 52: 2349
- 1m Demarteau J, Debuigne A, Detrembleur C. Chem. Rev. 2019; 119: 6906
- 2a Mazet C, Köhler V, Pfaltz A. Angew. Chem. Int. Ed. 2005; 44: 4888
- 2b Irmak M, Groschner A, Boysen MM. K. Chem. Commun. 2007; 177
- 3a Doyle MP, Davies SB, Hu W. Chem. Commun. 2000; 867
- 3b Lin W, Charette AB. Adv. Synth. Catal. 2005; 347: 1547
- 3c Marcoux D, Charette AB. Angew. Chem. Int. Ed. 2008; 47: 10155
- 3d Lindsay VN. G, Lin W, Charette AB. J. Am. Chem. Soc. 2009; 131: 16383
- 3e Marcoux D, Azzi S, Charette AB. J. Am. Chem. Soc. 2009; 131: 6970
- 3f Lindsay VN. G, Nicolas C, Charette AB. J. Am. Chem. Soc. 2011; 133: 8972
- 3g Lindsay VN. G, Fiset D, Gritsch PJ, Azzi S, Charette AB. J. Am. Chem. Soc. 2013; 135: 1463
- 3h Wang H, Guptill DM, Varela-Alvarez A, Musaev DG, Davies HM. L. Chem. Sci. 2013; 4: 2844
- 3i Rosenberg ML, Krivokapic A, Tilset M. Org. Lett. 2009; 11: 547
- 3j Rosenberg ML, Vlašaná K, Gupta NS, Wragg D, Tilset M. J. Org. Chem. 2011; 76: 2465
- 4a Che C.-M, Huang J.-S, Lee F.-W, Li Y, Lai T.-S, Kwong H.-L, Teng P.-F, Lee W.-S, Lo W.-C, Peng S.-M, Zhou Z.-Y. J. Am. Chem. Soc. 2001; 123: 4119
- 4b Miller JA, Gross BA, Zhuravel MA, Jin W, Nguyen ST. Angew. Chem. Int. Ed. 2005; 44: 3885
- 4c Gill CS, Venkatasubbaiah K, Jones CW. Adv. Synth. Catal. 2009; 351: 1344
- 4d Chanthamath S, Phomkeona K, Shibatomi K, Iwasa S. Chem. Commun. 2012; 48: 7750
- 4e Chanthamath S, Nguyen DT, Shibatomi K, Iwasa S. Org. Lett. 2013; 15: 772
- 4f Chanthamath S, Takaki S, Shibatomi K, Iwasa S. Angew. Chem. Int. Ed. 2013; 52: 5818
- 4g Nakagawa Y, Chanthamath S, Shibatomi K, Iwasa S. Org. Lett. 2015; 17: 2792
- 4h Xie M.-S, Zhou P, Niu H.-Y, Qu G.-R, Guo H.-M. Org. Lett. 2016; 18: 4344
- 5a Chen Y, Fields KB, Zhang XP. J. Am. Chem. Soc. 2004; 126: 14718
- 5b Chen Y, Ruppel JV, Zhang XP. J. Am. Chem. Soc. 2007; 129: 12074
- 5c Zhu S, Perman JA, Zhang XP. Angew. Chem. Int. Ed. 2008; 47: 8460
- 5d Zhu S, Ruppel JV, Lu H, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2008; 130: 5042
- 5e Zhu S, Xu X, Perman JA, Zhang XP. J. Am. Chem. Soc. 2010; 132: 12796
- 5f Lu H, Dzik WI, Xu X, Wojtas L, de Bruin B, Zhang XP. J. Am. Chem. Soc. 2011; 133: 8518
- 5g Das BG, Chirila A, Tromp M, Reek JN. H, de Bruin B. J. Am. Chem. Soc. 2016; 138: 8968
- 5h Jiang H, Lang K, Lu H, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2017; 139: 9164
- 5i Xu X, Wang Y, Cui X, Wojtas L, Zhang XP. Chem. Sci. 2017; 8: 4347
- 5j Wang Y, Wen X, Cui X, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2017; 139: 1049
- 5k Roy S, Das SK, Chattopadhyay B. Angew. Chem. Int. Ed. 2018; 57: 2238
- 6a Maas G, Alt M, Mayer D, Bergsträsser U, Sklenak S, Xavier P, Apeloig Y. Organometallics 2001; 20: 4607
- 6b Maas G, Daucher B, Maier A, Gettwert V. Chem. Commun. 2004; 238
- 6c Pastor-Pérez L, Wiebe C, Pérez-Prieto J, Stiriba S.-E. J. Org. Chem. 2007; 72: 1541
- 6d Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112
- 6e Hommelsheim R, Guo Y, Yang Z, Empel C, Koenigs RM. Angew. Chem. Int. Ed. 2019; 58: 1203
- 7a Hudlicky T, Olivo HF, Natchus MG, Umpierrez EF, Pandolfi E, Volonterio C. J. Org. Chem. 1990; 55: 4767
- 7b Jiang N, Qu Z, Wang J. Org. Lett. 2001; 3: 2989
- 7c Taber DF, Sheth RB, Joshi PV. J. Org. Chem. 2005; 70: 2851
- 7d Liu S, Jiang J, Chen J, Wei Q, Yao W, Xia F, Hu W. Chem. Sci. 2017; 8: 4312
- 7e Shang W, Duan D, Liu Y, Lv J. Org. Lett. 2019; 21: 8013
- 7f Zhukovsky D, Dar’in D, Kantin G, Krasavin M. Eur. J. Org. Chem. 2019; 2397
- 8a Lei T, Zhou C, Huang M.-Y, Zhao L.-M, Yang B, Ye C, Xiao H, Meng Q.-Y, Ramamurthy V, Tung C.-H, Wu L.-Z. Angew. Chem. Int. Ed. 2017; 56: 15407
- 8b Pagire SK, Hossain A, Traub L, Kerres S, Reiser O. Chem. Commun. 2017; 53: 12072
- 8c Daub ME, Jung H, Lee BJ, Won J, Baik M.-H, Yoon TP. J. Am. Chem. Soc. 2019; 141: 9543
- 9 Compound 5l is a known compound (see ref. 8a), hydrogens at C-1 and C-2 have been determined to be trans-selective by 1H NMR spectroscopy.
- 10 Under blue LED irradiation, the addition of Ir(ppy)3 photosensitizer gave similar performance as a single co-catalyst (Scheme 5 vs Table S7 in SI).
- 11 Li W, Wang J, Hu X, Shen K, Wang W, Chu Y, Lin L, Liu X, Feng X. J. Am. Chem. Soc. 2010; 132: 8532
- 12 Wang SC, Troast DM, Conda-Sheridan M, Zuo G, LaGarde D, Louie J, Tantillo DJ. J. Org. Chem. 2009; 74: 7822
- 13 Mato M, Herlé B, Echavarren AM. Org. Lett. 2018; 20: 4341
For selected reviews, see:
For recent selected examples of catalysis by copper, see:
For recent selected examples of catalysis by rhodium(II), see:
Catalysis by rhodium(I):
For recent selected examples of catalysis by ruthenium, see:
For recent selected examples of catalysis by cobalt, see: