Trisubstituted alkenes featuring aryl groups: stereoselective synthetic strategies and applications

Li J, Zhang Z, Wu L, Zhang W, Chen P, Lin Z, Liu G. Nature, 2019, 574: 516–521 Cuenca AB, Fernández E. Chem Soc Rev, 2021, 50: 72–86 Aïssa C. Eur J Org Chem, 2009, 2009: 1831–1844 Nguyen TT, Koh MJ, Mann TJ, Schrock RR, Hoveyda AH. Nature, 2017, 552: 347–354 Alisha M, Philip RM, Anilkumar G. Eur J Org Chem, 2022, 2022: e202101384 Neveselý T, Wienhold M, Molloy JJ, Gilmour R. Chem Rev, 2022, 122: 2650–2694 Bottcher SE, Hutchinson LE, Wilger DJ. Synthesis, 2020, 52: 2807–2820 Weiss J. Nature, 1943, 152: 176–178 Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ. Chem Commun, 2001, 1740–1741 Niu G, Zhang R, Shi X, Park H, Xie S, Kwok RTK, Lam JWY, Tang BZ. TrAC Trends Anal Chem, 2020, 123: 115769 Liu H, Xiong LH, Kwok RTK, He X, Lam JWY, Tang BZ. Adv Opt Mater, 2020, 8: 2000162 Gao M, Tang BZ. Coord Chem Rev, 2020, 402: 213076 Ding D, Li K, Liu B, Tang BZ. Acc Chem Res, 2013, 46: 2441–2453 Zhao Z, Zheng X, Du L, Xiong Y, He W, Gao X, Li C, Liu Y, Xu B, Zhang J, Song F, Yu Y, Zhao X, Cai Y, He X, Kwok RTK, Lam JWY, Huang X, Lee Phillips D, Wang H, Tang BZ. Nat Commun, 2019, 10: 2952 Mei J, Hong Y, Lam JWY, Qin A, Tang Y, Tang BZ. Adv Mater, 2014, 26: 5429–5479 Leung NLC, Xie N, Yuan W, Liu Y, Wu Q, Peng Q, Miao Q, Lam JWY, Tang BZ. Chem Eur J, 2014, 20: 15349–15353 Yan D, Wu Q, Wang D, Tang BZ. Angew Chem Int Ed, 2021, 60: 15724–15742 Buttard F, Sharma J, Champagne PA. Chem Commun, 2021, 57: 4071–4088 La DD, Bhosale SV, Jones LA, Bhosale SV. ACS Appl Mater Interfaces, 2018, 10: 12189–12216 Zhang M, Zhao W. Aggregate, 2021, 2: e60 Nakashima Y, Hirata G, Sheppard TD, Nishikata T. Asian J Org Chem, 2020, 9: 480–491 Nilsson P, Larhed M, Hallberg A. J Am Chem Soc, 2001, 123: 8217–8225 Liu Y, Li D, Park CM. Angew Chem, 2011, 123: 7471–7474 Tsai JJ, Huang YH, Chou CM. Org Lett, 2021, 23: 9468–9473 Oi S, Sakai K, Inoue Y. Org Lett, 2005, 7: 4009–4011 Ilies L, Asako S, Nakamura E. J Am Chem Soc, 2011, 133: 7672–7675 Wencel-Delord J, Nimphius C, Patureau FW, Glorius F. Chem Asian J, 2012, 7: 1208–1212 Song S, Lu P, Liu H, Cai SH, Feng C, Loh TP. Org Lett, 2017, 19: 2869–2872 Li T, Shen C, Sun Y, Zhang J, Xiang P, Lu X, Zhong G. Org Lett, 2019, 21: 7772–7777 Shibata T, Kojima M, Onoda S, Ito M. Org Lett, 2021, 23: 8158–8162 Li MY, Han P, Hu TJ, Wei D, Zhang G, Qin A, Feng CG, Tang BZ, Lin GQ. iScience, 2020, 23: 100966 Zhang SS, Hu TJ, Li MY, Song YK, Yang XD, Feng CG, Lin GQ. Angew Chem Int Ed, 2019, 58: 3387–3391 Li M, Wei D, Feng C, Lin G. Chem An Asian J, 2022, 17: e202200456 Nakashima Y, Matsumoto J, Nishikata T. ACS Catal, 2021, 11: 11526–11531 Chen Y, Wang J, Wu X, Zhu C. ACS Org Inorg Au, 2022, 2: 392–395 Su MD, Liu YF, Nie ZW, Yang TL, Cao ZZ, Li H, Luo WP, Liu Q, Guo CC. J Org Chem, 2022, 87: 7022–7032 Yadav AK, Sharma AK, Singh KN. Org Chem Front, 2019, 6: 989–993 Suga T, Takada R, Shimazu S, Sakata M, Ukaji Y. J Org Chem, 2022, 87: 7487–7493 Ren S, Fu J, Cheng D, Li X, Xu X. Tetrahedron Lett, 2021, 66: 152829 Wu K, Sun N, Hu B, Shen Z, Jin L, Hu X. Adv Synth Catal, 2018, 360: 3038–3043 Kortman GD, Hull KL. ACS Catal, 2017, 7: 6220–6224 Oh CH, Jung HH, Kim KS, Kim N. Angew Chem Int Ed, 2003, 42: 805–808 Lautens M, Yoshida M. Org Lett, 2002, 4: 123–125 Lautens M, Yoshida M. J Org Chem, 2003, 68: 762–769 Kim N, Kim KS, Gupta AK, Oh CH. Chem Commun, 2004, 618–619 Arcadi A, Aschi M, Chiarini M, Ferrara G, Marinelli F. Adv Synth Catal, 2010, 352: 493–498 Liu Z, Derosa J, Engle KM. J Am Chem Soc, 2016, 138: 13076–13081 Zhu H, Xing J, Wu C, Wang C, Yao W, Dou X. Org Lett, 2022, 24: 4896–4901 Cacchi S, Fabrizi G, Goggiamani A, Persiani D. Org Lett, 2008, 10: 1597–1600 Xue F, Zhao J, Hor TSA. Chem Commun, 2013, 49: 10121–10123 Gao K, Lee PS, Fujita T, Yoshikai N. J Am Chem Soc, 2010, 132: 12249–12251 Zhou W, Yang Y, Wang Z, Deng GJ. Org Biomol Chem, 2014, 12: 251–254 Zhang J, Shrestha R, Hartwig JF, Zhao P. Nat Chem, 2016, 8: 1144–1151 Chen H, Gao L, Liu X, Wang G, Li S. Eur J Org Chem, 2021, 2021: 5238–5242 Liu X, Li B, Liu Q. Synthesis, 2019, 51: 1293–1310 Larionov E, Li H, Mazet C. Chem Commun, 2014, 50: 9816–9826 Liu H, Cai C, Ding Y, Chen J, Liu B, Xia Y. ACS Omega, 2020, 5: 11655–11670 Zhao J, Cheng B, Chen C, Lu Z. Org Lett, 2020, 22: 837–841 Zhang S, Bedi D, Cheng L, Unruh DK, Li G, Findlater M. J Am Chem Soc, 2020, 142: 8910–8917 Xu S, Liu G, Huang Z. Chin J Chem, 2021, 39: 585–589 Xu S, Geng P, Li Y, Liu G, Zhang L, Guo Y, Huang Z. ACS Catal, 2021, 11: 10138–10147 Hu X, He JX, Zhang Y, Zhou J, Yu JS. Chin J Chem, 2021, 39: 2227–2233 Li G, Kuo JL, Han A, Abuyuan JM, Young LC, Norton JR, Palmer JH. J Am Chem Soc, 2016, 138: 7698–7704 Kapat A, Sperger T, Guven S, Schoenebeck F. Science, 2019, 363: 391–396 Zong Y, Ma Q, Tsui GC. Org Lett, 2021, 23: 6169–6173 Wang Y, Tang Y, Zong Y, Tsui GC. Org Lett, 2022, 24: 4087–4092 Thornbury RT, Toste FD. Angew Chem Int Ed, 2016, 55: 11629–11632 Zong Y, Tang Y, Tsui GC. Org Lett, 2022, 24: 6380–6385 Tian P, Feng C, Loh TP. Nat Commun, 2015, 6: 7472 Kong L, Liu B, Zhou X, Wang F, Li X. Chem Commun, 2017, 53: 10326–10329 Lu X, Wang Y, Zhang B, Pi JJ, Wang XX, Gong TJ, Xiao B, Fu Y. J Am Chem Soc, 2017, 139: 12632–12637 Nambo M, Ghosh K, Yim JCH, Tahara Y, Inai N, Yanai T, Crudden CM. ACS Catal, 2022, 12: 9526–9532 Ma Q, Liu C, Tsui GC. Org Lett, 2020, 22: 5193–5197 Tian H, Xia Q, Wang Q, Dong J, Liu Y, Wang Q. Org Lett, 2019, 21: 4585–4589 Cao CL, Zhang GX, Xue F, Deng HP. Org Chem Front, 2022, 9: 959–965 Domański S, Chaładaj W. ACS Catal, 2016, 6: 3452–3456 Zhu C, Yue H, Maity B, Atodiresei I, Cavallo L, Rueping M. Nat Catal, 2019, 2: 678–687 Zhu C, Yue H, Rueping M. Nat Commun, 2022, 13: 3240 Yang J, Chi Z, Zhu W, Tang BZ, Li Z. Sci China Chem, 2019, 62: 1090–1098 Yang J, Huang J, Li Q, Li Z. J Mater Chem C, 2016, 4: 2663–2684 Wang Y, Liu W, Qu Z, Tan H, Liu Y, Xie G, Zhu W. Dyes Pigments, 2017, 143: 173–182 Nie H, Chen B, Zeng J, Xiong Y, Zhao Z, Tang BZ. J Mater Chem C, 2018, 6: 3690–3698 Wang H, Liu G, Dong S, Xiong J, Du Z, Cheng X. J Mater Chem B, 2015, 3: 7401–7407 Yan L, Zhang Y, Xu B, Tian W. Nanoscale, 2016, 8: 2471–2487 Li D, Qin W, Xu B, Qian J, Tang BZ. Adv Mater, 2017, 29: 1703643 Qian J, Tang BZ. Chem, 2017, 3: 56–91 Zhou Y, Hua J, Tang BZ, Tang Y. Sci China Chem, 2019, 62: 1312–1332 Gogoi A, Mukherjee S, Ramesh A, Das G. Anal Chem, 2015, 87: 6974–6979 Hu J, Liu R, Zhai S, Wu Y, Zhang H, Cheng H, Zhu H. J Mater Chem C, 2017, 5: 11781–11789 Horak E, Hranjec M, Vianello R, Steinberg IM. Dyes Pigments, 2017, 142: 108–115 Pan S, Liu W, Tang J, Yang Y, Feng H, Qian Z, Zhou J. J Mater Chem B, 2018, 6: 3927–3933 Jiang Y, Li G, Che W, Liu Y, Xu B, Shan G, Zhu D, Su Z, Bryce MR. Chem Commun, 2017, 53: 3022–3025 Zhao Z, Gao S, Zheng X, Zhang P, Wu W, Kwok RTK, Xiong Y, Leung NLC, Chen Y, Gao X, Lam JWY, Tang BZ. Adv Funct Mater, 2018, 28: 1705609 Liu D, Li J, Liu J, Lu X, Hu M, Li Y, Shu Z, Ni Z, Ding S, Jiang L, Zhen Y, Zhang X, Dong H, Hu W. J Mater Chem C, 2018, 6: 3856–3860 Zhu M, Yang C. Chem Soc Rev, 2013, 42: 4963–4976 Im Y, Byun SY, Kim JH, Lee DR, Oh CS, Yook KS, Lee JY. Adv Funct Mater, 2017, 27: 1603007 Cai X, Su SJ. Adv Funct Mater, 2018, 28: 1802558 Lee JH, Chen CH, Lee PH, Lin HY, Leung M, Chiu TL, Lin CF. J Mater Chem C, 2019, 7: 5874–5888 Park H, Lee J, Kang I, Chu HY, Lee JI, Kwon SK, Kim YH. J Mater Chem, 2012, 22: 2695–2700 Chercka D, Yoo SJ, Baumgarten M, Kim JJ, Müllen K. J Mater Chem C, 2014, 2: 9083–9086 Sun W, Zhou N, Xiao Y, Wang S, Li X. Chem Asian J, 2017, 12: 3069–3076 Tang X, Bai Q, Shan T, Li J, Gao Y, Liu F, Liu H, Peng Q, Yang B, Li F, Lu P. Adv Funct Mater, 2018, 28: 1705813 Shellaiah M, Wu YH, Singh A, Ramakrishnam Raju MV, Lin HC. J Mater Chem A, 2013, 1: 1310–1318 Wang C, Li L, Zhan X, Ruan Z, Xie Y, Hu Q, Ye S, Li Q, Li Z. Sci Bull, 2016, 61: 1746–1755 Feng X, Xu Z, Hu Z, Qi C, Luo D, Zhao X, Mu Z, Redshaw C, Lam JWY, Ma D, Tang BZ. J Mater Chem C, 2019, 7: 2283–2290 Zhang H, Li A, Li G, Li B, Wang Z, Xu S, Xu W, Tang BZ. Adv Opt Mater, 2020, 8: 1902195 Wang H, Li Y, Zhang Y, Mei J, Su J. Chem Commun, 2019, 55: 1879–1882 Wang H, Gu X, Hu R, Lam JWY, Zhang D, Tang BZ. Chem Sci, 2016, 7: 5692–5698 Wang Y, Lv MZ, Song N, Liu ZJ, Wang C, Yang YW. Macromolecules, 2017, 50: 5759–5766 Li X, Li Z, Yang YW. Adv Mater, 2018, 30: 1800177 Zhang JC, Pan C, Zhu YF, Zhao LZ, He HW, Liu X, Qiu J. Adv Mater, 2018, 30: 1804644 Bian L, Shi H, Wang X, Ling K, Ma H, Li M, Cheng Z, Ma C, Cai S, Wu Q, Gan N, Xu X, An Z, Huang W. J Am Chem Soc, 2018, 140: 10734–10739 Tao Y, Chen R, Li H, Yuan J, Wan Y, Jiang H, Chen C, Si Y, Zheng C, Yang B, Xing G, Huang W. Adv Mater, 2018, 30: 1803856 Zhang J, Tian H. Adv Opt Mater, 2018, 6: 1701278 Wu NMW, Ng M, Yam VWW. Nat Commun, 2022, 13: 33 Wang S, Wang F, Li C, Li T, Cao D, Ma X. Sci China Chem, 2018, 61: 1301–1306 Zhao J, Chi Z, Yang Z, Mao Z, Zhang Y, Ubba E, Chi Z. Mater Chem Front, 2018, 2: 1595–1608 Yang Z, Chi Z, Mao Z, Zhang Y, Liu S, Zhao J, Aldred MP, Chi Z. Mater Chem Front, 2018, 2: 861–890 Pramanik S, Deol H, Bhalla V, Kumar M. ACS Appl Mater Interfaces, 2018, 10: 12112–12123 Roy B, Reddy MC, Hazra P. Chem Sci, 2018, 9: 3592–3606 Zhuang W, Xu Y, Li G, Hu J, Ma B, Yu T, Su X, Wang Y. ACS Appl Mater Interfaces, 2018, 10: 18489–18498 Mellerup SK, Wang S. Chem Soc Rev, 2019, 48: 3537–3549 Huang G, Jiang Y, Yang S, Li BS, Tang BZ. Adv Funct Mater, 2019, 29: 1900516 Zhang J, He B, Hu Y, Alam P, Zhang H, Lam JWY, Tang BZ. Adv Mater, 2021, 33: 2008071 Chen Z, Liu J, Chen Y, Zheng X, Liu H, Li H. ACS Appl Mater Interfaces, 2021, 13: 1353–1366 Yang Z, Chi Z, Yu T, Zhang X, Chen M, Xu B, Liu S, Zhang Y, Xu J. J Mater Chem, 2009, 19: 5541–5546 Ou D, Yu T, Yang Z, Luan T, Mao Z, Zhang Y, Liu S, Xu J, Chi Z, Bryce MR. Chem Sci, 2016, 7: 5302–5306 Wang L, Yu T, Xie Z, Chen X, Yang Z, Zhang Y, Aldred MP, Chi Z. J Mater Chem C, 2018, 6: 8832–8838 Luo M, Zhao J, Liu Y, Jiang L, Wang S, Chi Z. Adv Opt Mater, 2022, 10: 2201195 Li N, Gu Y, Chen Y, Zhang L, Zeng Q, Geng T, Wu L, Jiang L, Xiao G, Wang K, Zou B. J Phys Chem C, 2019, 123: 6763–6767 Wang C, Yu Y, Yuan Y, Ren C, Liao Q, Wang J, Chai Z, Li Q, Li Z. Matter, 2020, 2: 181–193 Yu T, Ou D, Wang L, Zheng S, Yang Z, Zhang Y, Chi Z, Liu S, Xu J, Aldred MP. Mater Chem Front, 2017, 1: 1900–1904 Jiang S, Liu S, Meng L, Qi Q, Wang L, Xu B, Liu J, Tian W. Sci China Chem, 2020, 63: 497–503 Tao T, Gan Y, Zhao Y, Yu J, Huang Q, Yang Z, Chen M, Huang W. J Mater Chem C, 2019, 7: 3765–3771 Kong TT, Zhao Z, Li Y, Wu F, Jin T, Tang BZ. J Mater Chem B, 2018, 6: 5986–5991 Yan M, Feng S, Yu L, Xue Y, Huang J, Yang X. Biosens Bioelectron, 2021, 192: 113532 Yao H, Dai J, Zhuang Z, Yao J, Wu Z, Wang S, Xia F, Zhou J, Lou X, Zhao Z. Sci China Chem, 2020, 63: 1815–1824 Wang S, Chen C, Wu J, Zhang J, Lam JWY, Wang H, Chen L, Tang BZ. Sci China Chem, 2022, 65: 870–876 Li Y, Zhao Z, Zhang J, Kwok RTK, Xie S, Tang R, Jia Y, Yang J, Wang L, Lam JWY, Zheng W, Jiang X, Tang BZ. Adv Funct Mater, 2018, 28: 1804632