REVIEWS

Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide

  • Chen-Long Li ,
  • Zhi-Xiang Yu
Expand
  • Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
* E-mail:

Received date: 2023-10-05

  Revised date: 2023-11-28

  Online published: 2023-12-08

Supported by

National Natural Science Foundation of China(21933003)

Abstract

Transition-metal-catalyzed cycloadditions have been evolved as important and efficient methods to construct cyclic molecules. Among them, transition-metal-catalyzed cycloadditions using carbon monoxide (CO) gas as the 1C synthon provide their unique and powerful approaches to build various cyclic molecules within a carbonyl group, which either acts as an important functional group within the cycloadducts, or can be further elaborated to other functional groups. The tremendous advances in this field are introduced.

Cite this article

Chen-Long Li , Zhi-Xiang Yu . Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide[J]. Chinese Journal of Organic Chemistry, 2024 , 44(4) : 1045 -1068 . DOI: 10.6023/cjoc202310003

References

[1]
Jiao L.; Yu Z.-X. J. Org. Chem. 2013, 78, 6842.
[2]
Gao Y.; Fu X.-F.; Yu Z.-X. Top. Curr. Chem. 2014, 346, 195.
[3]
Chen P.-H.; Billett B. A.; Tsukamoto T.; Dong G. ACS Catal. 2017, 7, 1340.
[4]
Fumagalli G.; Stanton S.; Bower J. F. Chem. Rev. 2017, 117, 9404.
[5]
Liu J.; Liu R.; Wei Y.; Shi M. Trends Chem. 2019, 1, 779.
[6]
Wang J.; Blaszczyk S. A.; Li X.; Tang W. Chem. Rev. 2021, 121, 110.
[7]
Zhang Q.; Kang J.; Wang Y. ChemCatChem 2010, 2, 1030.
[8]
Shahabuddin M.; Alam M. T.; Krishna B. B.; Thallada Bhaskar T.; Perkins G. Bioresour. Technol. 2020, 312, 123596.
[9]
dos Santos R. G.; Alencar A. C. Int. J. Hydrogen Energy 2020, 45, 18114.
[10]
Franke R.; Selent D.; B?rner A. Chem. Rev. 2012, 112, 5675.
[11]
Wu X.-F.; Fang X.; Wu L.; Jackstell R.; Neumann H.; Beller M. Acc. Chem. Res. 2014, 47, 1041.
[12]
Wu L.; Liu Q.; Jackstell R.; Bellerm M. Angew. Chem., Int. Ed. 2014, 53, 6310.
[13]
Yin Z.; Wang Z.; Wu X.-F. Chin. J. Org. Chem. 2019, 39, 573. (in Chinese)
[13]
(尹志平, 王泽超, 吴小锋, 有机化学, 2019, 39, 573.)
[14]
Feng T.; Du J.; Yan W.; Li X.; Gao W.; Chang H.; Wei W. Chin. J. Org. Chem. 2019, 39, 1197. (in Chinese)
[14]
(冯涛, 杜佳, 闫文静, 李兴, 高文超, 常宏宏, 魏文珑, 有机化学, 2019, 39, 1197.)
[15]
Wang P.; Yang D.; Liu H. Chin. J. Org. Chem. 2021, 41, 3448. (in Chinese)
[15]
(王鹏, 杨妲, 刘欢, 有机化学, 2021, 41, 3448.)
[16]
Wang Y.; Yu Z.-X. Acc. Chem. Res. 2015, 48, 2288.
[17]
Song W.; Blaszczyk S. A.; Liu J.; Wang S.; Tang W. Org. Biomol. Chem. 2017, 15, 7490.
[18]
Sato H.; Turnbull B. W. H.; Fukaya K.; Krische M. J. Angew. Chem., Int. Ed. 2018, 57, 3012.
[19]
Doerksen R. S.; Hodík T.; Hu G.; Huynh N. O.; Shuler W. G.; Krische M. J. Chem. Rev. 2021, 121, 4045.
[20]
Wang L.-N.; Yu Z.-X. Chin. J. Org. Chem. 2020, 40, 3536. (in Chinese)
[20]
(王路宁, 余志祥, 有机化学, 2020, 40, 3536.)
[21]
Trost B. M. Angew. Chem., Int. Ed. Engl. 1995, 90, 259.
[22]
Sheldon R. A. Pure Appl. Chem. 2000, 72, 1233.
[23]
Wender P. A.; Miller B. L. In Organic Synthesis: Theory & Applications, Vol. 2, Ed.: Hudlicky, T., JAI, Greenwich, 1993, p. 27.
[24]
Wender P. A.; Handy S. T.; Wright D. L. Chem. Ind. (Chichester, U. K.) 1997, 765.
[25]
Wender P. A.; Bi F. C.; Gamber G. G.; Gosselin F.; Hubbard R. D.; Scanio M. J. C.; Sun R.; Williams T. J.; Zhang L. Pure Appl. Chem. 2002, 74, 25.
[26]
Mondal K.; Halder P.; Gopalan G.; Sasikumar P.; Radhakrishnan K. V.; Das P. Org. Biomol. Chem. 2019, 17, 5212.
[27]
Hussain N.; Chhalodia A. K.; Ahmed A.; Mukherjee D. ChemistrySelect 2020, 5, 11272.
[28]
Chen Z.; Wang L.-C.; Wu X.-F. Chem. Commun. 2020, 56, 6016.
[29]
Khedkar M. V.; Khan S. R.; Lambat T. L.; Chaudhary R. G.; Abdala A. A. Curr. Org. Chem. 2020, 24, 2588.
[30]
Tan Y.; Lang J.; Tang M.; Li J.; Mi P.; Zheng X. ChemistrySelect 2021, 6, 2343.
[31]
Alcaide B.; Almendros P. Eur. J. Org. Chem. 2004, 2004, 3377.
[32]
Shibata T. Adv. Synth. Catal. 2006, 348, 2328.
[33]
Park J. H.; Chang K.-M.; Chung Y. K. Coord. Chem. Rev. 2009, 253, 2461.
[34]
Hanson B. E. Comments Inorg. Chem. 2002, 23, 289.
[35]
Kitagaki S.; Inagaki F.; Mukai C. Chem. Soc. Rev. 2014, 43, 2956.
[36]
Nakamura I.; Yamamoto Y. Chem. Rev. 2004, 104, 2127.
[37]
Vizer S. A.; Yerzhanov K. B.; Quntar A. A. A. A.; Dembitsky V. M. Tetrahedron 2004, 60, 5499.
[38]
Omae I. Coord. Chem. Rev. 2011, 255, 139.
[39]
Wender P. A.; Deschamps N. M.; Gamber G. G. Angew. Chem., Int. Ed. 2003, 42, 1853.
[40]
Wender P. A.; Deschamps N. M.; Williams T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
[41]
Wender P. A.; Croatt M. P.; Deschamps N. M. J. Am. Chem. Soc. 2004, 126, 5948.
[42]
Pitcock W. H. Jr.; Lord R. L.; Baik M.-H. J. Am. Chem. Soc. 2008, 130, 5821.
[43]
Croatt M. P.; Wender P. A. Eur. J. Org. Chem. 2010, 2010, 19.
[44]
Wender P. A.; Croatt M. P.; Deschamps N. M. Angew. Chem., Int. Ed. 2006, 45, 2459.
[45]
Yuan W.; Dong X.; Shi M.; McDowell P.; Li G. Org. Lett. 2012, 14, 5582.
[46]
Chen G.-Q.; Shi M. Chem. Commun. 2013, 49, 698.
[47]
Chen G.-Q.; Zhang X.-N.; Wei Y.; Tang X.-Y.; Shi M. Angew. Chem., Int. Ed. 2014, 53, 8492.
[48]
Chen G.-Q.; Tang X.-Y.; Shi M. Synlett 2014, 25, 2311.
[49]
Hoshimoto Y.; Ashida K.; Sasaoka Y.; Kumar R.; Kamikawa K.; Verdaguer X.; Riera A.; Ohashi M.; Ogoshi S. Angew. Chem., Int. Ed. 2017, 56, 8206.
[50]
Ashida K.; Hoshimoto Y.; Tohnai N.; Scott D. E.; Ohashi M.; Imaizumi H.; Tsuchiya Y.; Ogoshi S. J. Am. Chem. Soc. 2020, 142, 1594.
[51]
Ashida K.; Hoshimoto Y.; Ogoshi S. Synlett 2021, 32, 1537.
[52]
Suzuki N.; Kondo T.; Mitsudo T. Organometallics 1998, 17, 766.
[53]
Wang C.; Wu Y.-D. Organometallics 2008, 27, 6152.
[54]
Fukuyama T.; Yamaura R.; Higashibeppu Y.; Okamura T.; Ryu I.; Kondo T.; Mitsudo T. Org. Lett. 2005, 7, 5781.
[55]
Kondo T.; Kaneko Y.; Taguchi Y.; Nakamura A.; Okada T.; Shiotsuki M.; Ura Y.; Wada K.; Mitsudo T. J. Am. Chem. Soc. 2002, 124, 6824.
[56]
Huang Q.; Hua R. Chem.-Eur. J. 2007, 13, 8333.
[57]
Ojima I.; Lee S.-Y. J. Am. Chem. Soc. 2000, 122, 2385.
[58]
Bennacer B.; Fujiwara M.; Lee S.-Y.; Ojima I. J. Am. Chem. Soc. 2005, 127, 17756.
[59]
Bennacer B.; Fujiwara M.; Ojima I. Org. Lett. 2004, 6, 3589.
[60]
Kaloko J. J.; Teng Y.-H. G.; Ojima I. Chem. Commun. 2009, 4569.
[61]
Chien C.-W.; Teng Y.-H. G.; Honda T.; Ojima I. J. Org. Chem. 2018, 83, 11623.
[62]
Teng Y.-H. G.; Chien C.-W.; Chiou W.-H.; Honda T.; Ojima I. Front. Chem. 2018, 6, 401.
[63]
Salacz L.; Girard N.; Blond G.; Suffert J. Org. Lett. 2018, 20, 3915.
[64]
Salacz L.; Girard N.; Suffert J.; Blond G. Molecules 2019, 24, 595.
[65]
Church T. L.; Getzler Y. D. Y. L.; Byrne C. M.; Coates G. M. Chem. Commun. 2007, 657.
[66]
Ojima I.; Athan A.; Commandeur C.; Chiou W.-H. Amidocarbonylation, Cyclohydrocarbonylation, and Related Reactions, Elsevier Inc, Philadelphia, 2013.
[67]
Waser J. Top. Heterocycl. Chem. 2013, 32, 225.
[68]
Kramer J. W.; Rowley J. M.; Coates G. W. Org. React. 2015, 86, 1.
[69]
Couty F.; David O. R. P. Top. Heterocycl. Chem. 2016, 41, 1.
[70]
Kurahashi T.; de Meijere A. Angew. Chem., Int. Ed. 2005, 44, 7881.
[71]
Hidai M.; Orisaku M.; Uchida Y. Chem. Lett. 1980, 9, 753.
[72]
Xu W.-B.; Li C.; Wang J. Chem.-Eur. J. 2018, 24, 15786.
[73]
Fukuyama T.; Higashibeppu Y.; Yamaura R.; Ryu I. Org. Lett. 2007, 9, 587.
[74]
Koga Y.; Narasaka K. Chem. Lett. 1999, 28, 705.
[75]
Jiao L.; Lin M.; Zhuo L.-G.; Yu Z.-X. Org. Lett. 2010, 12, 2528.
[76]
Zhang G.-Y.; Lin M.; Yu Z.-X. Chem.-Asian J. 2023, 18, e202300032.
[77]
Feng Y.; Yu Z.-X. J. Org. Chem. 2015, 80, 1952.
[78]
Bose S.; Yang J.; Yu Z.-X. J. Org. Chem. 2016, 81, 6757.
[79]
Yang J.; Xu W.; Cui Q.; Fan X.; Wang L.-N.; Yu Z.-X. Org. Lett. 2017, 19, 6040.
[80]
Zhou Y.; Qin J.-L.; Xu W.; Yu Z.-X. Org. Lett. 2022, 24, 5902.
[81]
Wang J.; Hong B.; Hu D.; Kadonaga Y.; Tang R.; Lei X. J. Am. Chem. Soc. 2020, 142, 2238.
[82]
Li C.; Zhang H.; Feng J.; Zhang Y.; Wang J. Org. Lett. 2010, 12, 3082.
[83]
Lee S. l.; Park J. H.; Chung Y. K.; Lee S.-G. J. Am. Chem. Soc. 2004, 126, 2714.
[84]
Zhang W.; Zhang J. Org. Lett. 2011, 13, 688.
[85]
Liu B.-L.; Wei Y.; Shi M. Organometallics 2012, 31, 4601.
[86]
Mazumder S.; Shang D.; Negru D. E.; Baik M.-H.; Evans P. A. J. Am. Chem. Soc. 2012, 134, 20569.
[87]
Evans P. A.; Burnie A. J.; Negru D. E. Org. Lett. 2014, 16, 4356.
[88]
Kim S.; Chung Y. K. Org. Lett. 2014, 16, 4352.
[89]
Burnie A. J.; Evans P. A. Chem. Commun. 2018, 54, 7621.
[90]
Shaw M. H.; Melikhova E. Y.; Kloer D. P.; Whittingham W. G.; Bower J. F. J. Am. Chem. Soc. 2013, 135, 4992.
[91]
Shaw M. H.; McCreanor N. G.; Whittingham W. G.; Bower J. F. J. Am. Chem. Soc. 2015, 137, 463.
[92]
Shaw M. H.; Whittingham W. G.; Bower J. F. Tetrahedron 2016, 72, 2731.
[93]
Wang G.-W.; McCreanor N. G.; Shaw M. H.; Whittingham W. G.; Bower J. F. J. Am. Chem. Soc. 2016, 138, 13501.
[94]
Dalling A. G.; Yamauchi T.; McCreanor N. G.; Cox L.; Bower J. F. Angew. Chem., Int. Ed. 2019, 58, 221.
[95]
Sokolova O, O.; Bower, J. F. Angew. Chem., Int. Ed. 2022, 61, e202205007.
[96]
Eaton B. E.; Rollman B.; Kaduk J. A. J. Am. Chem. Soc. 1992, 114, 6245.
[97]
Sigman M. S.; Eaton B. E. J. Am. Chem. Soc. 1996, 118, 11783.
[98]
Sigman M. S.; Kerr C. E.; Eaton B. E. J. Am. Chem. Soc. 1993, 115, 7545.
[99]
Sigman M. S.; Eaton B. E.; Heise J. D.; Kubiak C. P. Organometallics 1996, 15, 2829.
[100]
Sigman M. S.; Eaton B. E. J. Org. Chem. 1994, 59, 7488.
[101]
Morimoto T.; Chatani N.; Murai S. J. Am. Chem. Soc. 1999, 121, 1758.
[102]
Heldeweg R. F.; Hogeveen H. J. Am. Chem. Soc. 1976, 98, 6040.
[103]
Matsuda T.; Tsuboi T.; Murakami M. J. Am. Chem. Soc. 2007, 129, 12596.
[104]
Matsuda T.; Fukuhara K.; Yonekubo N.; Oyama S. Chem. Lett. 2017, 46, 1721.
[105]
Murakami M.; Itami K.; Ito Y. Angew. Chem., Int. Ed. Engl. 1996, 34, 2691.
[106]
Murakami M.; Itami K.; Ito Y. Organometallics 1999, 18, 1326.
[107]
Murakami M.; Itami K.; Ito Y. J. Am. Chem. Soc. 1997, 119, 2950.
[108]
Murakami M.; Itami K.; Ito Y. J. Am. Chem. Soc. 1999, 121, 4130.
[109]
Meng Q.; Li M.; Zhang J. J. Mol. Struct.: THEOCHEM 2005, 726, 47.
[110]
Mazumder S.; Crandell D. W.; Lord R. L.; Baik M.-H. J. Am. Chem. Soc. 2014, 136, 9414.
[111]
Yang Y.; Li H.-X.; Zhu T.-Y.; Zhang Z.-Y.; Yu Z.-X. J. Am. Chem. Soc. 2023, 145, 17087.
[112]
Zhang Y.; Chen Z.; Xiao Y.; Zhang J. Chem.-Eur. J. 2009, 15, 5208.
[113]
Wang T.; Wang C.-H.; Zhang J. Chem. Commun. 2011, 47, 5578.
[114]
Fukuyama T.; Ohta Y.; Brancour C.; Miyagawa K.; Ryu I.; Dhimane A. L.; Fensterbank L.; Malacria M. Chem.-Eur. J. 2012, 18, 7243.
[115]
Coskun D.; Tüzün N. ?. J. Organomet. Chem. 2017, 851, 97.
[116]
Li X.; Huang S.; Schienebeck C. M.; Shu D.; Tang W. Org. Lett. 2012, 14, 1584.
[117]
Chen W.; Tay J.-H.; Yu X.-Q.; Pu L. J. Org. Chem. 2012, 77, 6215.
[118]
Zhang Y.; Zhao G.; Pu L. Eur. J. Org. Chem. 2017, 2017, 7026.
[119]
Yang J.; Zhang P.; Shen Z.; Zhou Y.; Yu Z.-X. Chem 2023, 9, 1477.
[120]
Yang J.; Zhang P.; Shen Z.; Yu Z.-X. Chem.-Eur. J. 2023, doi: 10.1002/chem.202303407.
[121]
Tian Z.-Y.; Cui Q.; Liu C.-H.; Yu Z.-X. Angew. Chem., Int. Ed. 2018, 57, 15544.
[122]
Yang Y.; Tian Z.-Y.; Li C.-L.; Yu Z.-X. J. Org. Chem. 2022, 87, 10576.
[123]
Cui Q.; Tian Z.-Y.; Yu Z.-X. Chem.-Eur. J. 2021, 27, 5638.
[124]
Li C.-L.; Yang Y.; Zhou Y.; Duan Z.-C.; Yu Z.-X. J. Am. Chem. Soc. 2023, 145, 5496.
[125]
Murakami M.; Itami K.; Ito Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
[126]
Iwasuwa N.; Owada Y.; Matsuo T. Chem. Lett. 1995, 24, 115.
[127]
Owada Y.; Matsuo T.; Iwasuwa N. Tetrahedron 1997, 53, 11069.
[128]
Kurahashi T.; de Meijere A. Synlett 2005, 2005, 2619.
[129]
Liu C.-H.; Zhuang Z.; Bose S.; Yu Z.-X. Tetrahedron 2016, 72, 2752, and references therein.
[130]
Kamitani A.; Chatani N.; Morimoto T.; Murai S. J. Org. Chem. 2000, 65, 9230.
[131]
Cho S. H.; Liebeskind L. S. J. Org. Chem. 1987, 52, 2631.
[132]
Jiang G.-J.; Fu X.-F.; Li Q.; Yu Z.-X. Org. Lett. 2012, 14, 692.
[133]
Wang L.-N.; Cui Q.; Yu Z.-X. J. Org. Chem. 2016, 81, 10165.
[134]
Liu C.-H.; Yu Z.-X. Org. Biomol. Chem. 2016, 14, 5945.
[135]
Zhuang Z.; Li C.-L.; Xiang Y.; Wang Y.-H.; Yu Z.-X. Chem. Commun. 2017, 53, 2158.
[136]
Lin M.; Li F.; Jiao L.; Yu Z.-X. J. Am. Chem. Soc. 2011, 133, 1690.
[137]
Brancour C.; Fukuyama T.; Ohta Y.; Ryu I.; Dhimane A.-L.; Fensterbank L.; Malacria M. Chem. Commun. 2010, 46, 5470.
[138]
Schienebeck C. M.; Song W.; Smits A. M.; Tang W. Synthesis 2015, 47, 1076.
[139]
Ke X.-N.; Schienebeck C. M.; Zhou C.-C.; Xu X.-F.; Tang W.-P. Chin. Chem. Lett. 2015, 26, 730.
[140]
Shu D.; Li X.; Zhang M.; Robichaux P. J.; Tang W. Angew. Chem., Int. Ed. 2011, 50, 1346.
[141]
Shu D.; Li X.; Zhang M.; Robichaux P. J.; Guzei I. A.; Tang W. J. Org. Chem. 2012, 77, 6463.
[142]
Zhang M.; Tang W. Org. Lett. 2012, 14, 3756.
[143]
Li X.; Xie H.; Fu X.; Liu J.-T.; Wang H.-Y.; Xi B.-M.; Liu P.; Xu X.; Tang W. Chem.-Eur. J. 2016, 22, 10410.
[144]
Liu J.-T.; Simmons C. J.; Xie H.; Yang F.; Zhao X.-L.; Tang Y.; Tang W. Adv. Synth. Catal. 2017, 359, 693.
[145]
Li X.; Song W.; Tang W. J. Am. Chem. Soc. 2013, 135, 16797.
[146]
Song W.; Li X.; Yang K.; Zhao X.-L.; Glazier D. A.; Xi B.-M.; Tang W. J. Org. Chem. 2016, 81, 2930.
[147]
Fontana F.; Tron G. C.; Barbero N.; Ferrini S.; Thomas S. P.; Aggarwal V. K. Chem. Commun. 2010, 46, 267.
[148]
Murakami M.; Itami K.; Ubukata M.; Tsuji I.; Ito Y. J. Org. Chem. 1998, 63, 4.
[149]
Wender P. A.; Gamber G. G.; Hubbard R. D.; Zhang L. J. Am. Chem. Soc. 2002, 124, 2876.
[150]
Wegner H. A.; de Meijere A.; Wender P. A. J. Am. Chem. Soc. 2005, 127, 6530.
[151]
Wang Y.; Wang J.; Su J.; Huang F.; Jiao L.; Liang Y.; Yang D.; Zhang S.; Wender P. A.; Yu Z.-X. J. Am. Chem. Soc. 2007, 129, 10060.
[152]
Wang Y.; Liao W.; Wang Y.; Jiao L.; Yu Z.-X. J. Am. Chem. Soc. 2022, 144, 2624.
[153]
Jiao L.; Yuan C.; Yu Z.-X. J. Am. Chem. Soc. 2008, 130, 4421.
[154]
Yuan C.; Jiao L.; Yu Z.-X. Tetrahedron Lett. 2010, 51, 5674.
[155]
Fan X.; Tang M.-X.; Zhuo L.-G.; Tu Y. Q.; Yu Z.-X. Tetrahedron Lett. 2009, 50, 155.
[156]
Fan X.; Zhuo L.-G.; Tu Y. Q.; Yu Z.-X. Tetrahedron 2009, 65, 4709.
[157]
Liang Y.; Jiang X.; Yu Z.-X. Chem. Commun. 2011, 47, 6659.
[158]
Liang Y.; Jiang X.; Fu X.-F.; Ye S.; Wang T.; Yuan J.; Wang Y.; Yu Z.-X. Chem.-Asian J. 2012, 7, 593.
[159]
Huang F.; Yao Z.-K.; Wang Y.; Wang Y.; Zhang J.; Yu Z.-X. Chem.-Asian J. 2010, 5, 1555.
[160]
Liu J.; Zhou Y.; Zhu J.; Yu Z.-X. Org. Lett. 2021, 23, 7566.
[161]
Liu J.; Zhou Y.; Yu Z.-X. Org. Lett. 2022, 24, 1444.
[162]
Wang L.-N.; Huang Z.; Yu Z.-X. Cell Rep. Phys. Sci. 2023, 4, 101302.
[163]
Wang L.-N.; Huang Z.; Yu Z.-X. Org. Lett. 2023, 25, 1732.
[164]
Wender P. A.; Gamber G. G.; Hubbard R. D.; Pham S. M.; Zhang L. J. Am. Chem. Soc. 2005, 127, 2836.
[165]
Mbaezue I. I.; Ylijoki K. E. O. Organometallics 2017, 36, 2832.
[166]
Wender P. A.; Deschamps N. M.; Sun R. Angew. Chem., Int. Ed. 2006, 45, 3957.
[167]
Kim S. Y.; Lee S. I.; Choi S. Y.; Chung Y. K. Angew. Chem., Int. Ed. 2008, 47, 4914.
[168]
McCreanor N. G.; Stanton S.; Bower J. F. J. Am. Chem. Soc. 2016, 138, 11465.
[169]
Wang G.-W.; Sokolova O. O.; Young T. A.; Christodoulou E. M. S.; Butts C. P.; Bower J. F. J. Am. Chem. Soc. 2020, 142, 19006.
[170]
Wang G.-W.; Bower J. F. J. Am. Chem. Soc. 2018, 140, 2743.
[171]
Li C.-L.; Yang Y.; Zhou Y.; Yu Z.-X. Asian J. Org. Chem. 2022, 11, e202100571.
[172]
Yao Z.-K.; Li J.; Yu Z.-X. Org. Lett. 2011, 13, 134.
[173]
Fu X.-F.; Xiang Y.; Yu Z.-X. Chem.-Eur. J. 2015, 21, 4242.
[174]
Huang Z.; Wang X.; Jin Y.; Wang Z.; Yu Z.-X. Org. Lett. 2023, 25, 8829.
[175]
Shaw M. H.; Croft R. A.; Whittingham W. G.; Bower J. F. J. Am. Chem. Soc. 2015, 137, 8054.
[176]
Lv S.; Xu Y.; Li J. Tetrahedron 2018, 74, 6475.
[177]
Boyd O.; Wang G.-W.; Sokolova O. O.; Calow A. D. J.; Bertrand S. M.; Bower J. F. Angew. Chem., Int. Ed. 2019, 58, 18844.
[178]
Wang G.-W.; Boyd O.; Young T. A.; Bertrand S. M.; Bower J. F. J. Am. Chem. Soc. 2020, 142, 1740.
[179]
Wu X.; Wang C.; Liu N.; Qu J.; Chen Y. Nat. Commun. 2023, 14, 6960.
[180]
Yan M.; Kawamata Y.; Baran P. S. Chem. Rev. 2017, 117, 13230.
[181]
Wiebe A.; Gieshoff T.; M?hle S.; Rodrigo E.; Zirbes M.; Wald- vogel S. R. Angew. Chem., Int. Ed. 2018, 57, 5594.
[182]
M?hle S.; Zirbes M.; Rodrigo E.; Gieshoff T.; Wiebe A.; Wald- vogel S. R. Angew. Chem., Int. Ed. 2018, 57, 6018.
[183]
Novaes L. F. T.; Liu J.; Shen Y.; Lu L.; Meinhardt J. M.; Lin S. Chem. Soc. Rev. 2021, 50, 7941.
[184]
Goddard J.-P.; Ollivier C.; Fensterbank L. Acc. Chem. Res. 2016, 49, 1924.
[185]
Staveness D.; Bosque I.; Stephenson C. R. J. Acc. Chem. Res. 2016, 49, 2295.
[186]
Shaw M. H.; Twilton J.; MacMillan D. W. C. J. Org. Chem. 2016, 81, 6898.
[187]
Strieth-Kalthoff F.; James M. J.; Teders M.; Pitzer L.; Glorius F. Chem. Soc. Rev. 2018, 47, 7190.
[188]
Swords W. B.; Yoon T. P. In Specialist Periodical Reports: Photochemistry, Vol. 50, Eds.: Crespi, S.; Protti, S., Royal Society of Chemistry, Corydon, 2023, p. 428.
Outlines

/

〈 〉