C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives

Abstract

Chemoselective cross-coupling of phenol derivatives is valuable for generating products that retain halides. Here we discuss recent developments in selective cross-couplings of chloroaryl phenol derivatives, with a particular focus on reactions of chloroaryl tosylates. The first example of a C–O-selective Ni-catalyzed Suzuki–Miyaura coupling of chloroaryl tosylates is discussed in detail.

1 Introduction

2 Density Functional Theory Studies on Oxidative Addition at Nickel(0)

3 Stoichiometric Oxidative Addition Studies

4 Development of a Tosylate-Selective Suzuki Coupling

5 Conclusion and Outlook

Key words

nickel catalysis - cross-coupling - oxidative addition - chemoselectivity - density functional theory - Suzuki–Miyaura coupling

Publication History

Received: 27 April 2021

Accepted: 08 May 2021

Accepted Manuscript online:
08 May 2021

Article published online:
16 June 2021

• References and Notes

• 1 Qiu Z, Li C.-J. Chem. Rev. 2020; 120: 10454
• 2 Snieckus V. Chem. Rev. 1990; 90: 879
• 3 Nguyen HN, Huang X, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 11818
• 4 Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
• 5 Jiang S, Zhang L, Cui D, Yao Z, Gao B, Lin J, Wei D. Sci. Rep. 2016; 6: 34750
• 6 Hernandes MZ, Cavalcanti SM. T, Moreira DR. M, de Azevedo WF. Jr, Leite AC. L. Curr. Drug Targets 2010; 11: 303
• 7 Fang W.-Y, Ravindar L, Rakesh KP, Manukumar HM, Shantharam CS, Alharbi NS, Qin H.-L. Eur. J. Med. Chem. 2019; 173: 117
• 8 Lumefantrine and felodipine are FDA-approved; MK-0686 is an investigational drug, see: Kuduk SD, Di Marco CN, Chang RK, Wood MR, Schirripa KM, Kim JJ, Wai JM. C, DiPardo RM, Murphy KL, Ransom RW, Harrell CM, Reiss DR, Holahan MA, Cook J, Hess JF, Sain N, Urban MO, Tang C, Prueksaritanont T, Pettibone DJ, Bock MG. J. Med. Chem. 2007; 50: 272

For examples, see:
• 9a Echavarren AM, Stille JK. J. Am. Chem. Soc. 1987; 109: 5478
• 9b Kamikawa T, Hayashi T. Tetrahedron Lett. 1997; 38: 7087
• 9c Espino G, Kurbangalieva A, Brown JM. Chem. Commun. 2007; 1742
• 9d Hassan Z, Hussain M, Villinger A, Langer P. Tetrahedron 2012; 68: 6305
• 9e Shen C, Wei Z, Jiao H, Wu X.-F. Chem. Eur. J. 2017; 23: 13369
• 9f Kalvet I, Sperger T, Scattolin T, Magnin G, Schoenebeck F. Angew. Chem. Int. Ed. 2017; 56: 7078
• 9g Keaveney ST, Kundu G, Schoenebeck F. Angew. Chem. Int. Ed. 2018; 57: 12573

For Cl vs. OTf selectivity using Pd and phosphine ligands, see:
• 10a Littke AF, Dai C, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020
• 10b Schoenebeck F, Houk KN. J. Am. Chem. Soc. 2010; 132: 2496
• 10c Niemeyer ZL, Milo A, Hickey DP, Sigman MS. Nat. Chem. 2016; 8: 610
• 10d Reeves EK, Bauman OR, Mitchem GB, Neufeldt SR. Isr. J. Chem. 2020; 60: 406
• 11 For Cl vs. OTf selectivity using Pd and N-heterocyclic carbene ligands, see: Reeves EK, Humke JN, Neufeldt SR. J. Org. Chem. 2019; 84: 11799
• 12 For a review, see: Reeves EK, Entz ED, Neufeldt SR. Chem. Eur. J. 2021; 27: 6161
• 13 Entz ED, Russell JE. A, Hooker LV, Neufeldt SR. J. Am. Chem. Soc. 2020; 142: 15454
• 14a Zhang L, Meng T, Wu J. J. Org. Chem. 2007; 72: 9346
• 14b Ackermann L, Potukuchi HK, Althammer A, Born R, Mayer P. Org. Lett. 2010; 12: 1004
• 14c Wang Z.-Y, Chen G.-Q, Shao L.-X. J. Org. Chem. 2012; 77: 6608
• 14d Chen X, Ke H, Zou G. ACS Catal. 2014; 4: 379
• 15a Martín R, Buchwald SL. Angew. Chem. Int. Ed. 2007; 46: 7236
• 15b Ackermann L, Vicente R, Born R. Adv. Synth. Catal. 2008; 350: 741
• 15c Yi Z, Aschenaki Y, Daley R, Davick S, Schnaith A, Wander R, Kalyani D. J. Org. Chem. 2017; 82: 6946
• 16a Shang R, Ji D.-S, Chu L, Fu Y, Liu L. Angew. Chem. Int. Ed. 2011; 50: 4470
• 16b Shang R, Huang Z, Chu L, Fu Y, Liu L. Org. Lett. 2011; 13: 4240
• 17 Zhang L, Wu J. J. Am. Chem. Soc. 2008; 130: 12250
• 18a Hao CY, Wang D, Li YW, Dong LL, Jin Y, Zhang XR, Zhua HY, Chang S. RSC Adv. 2016; 6: 86502
• 18b Tang Y, Yang F, Nie S, Wang L, Luo Z, Lu H. Youji Huaxue 2015; 35: 705
• 19a Limmert ME, Roy AH, Hartwig JF. J. Org. Chem. 2005; 70: 9364
• 19b Ackermann L, Althammer A. Org. Lett. 2006; 8: 3457
• 19c He X.-Y, Zhang Z.-X, Li C.-J, Li Y. Russ. J. Gen. Chem. 2019; 89: 2591
• 20 Ohgi A, Semba K, Hiyama T, Nakao Y. Chem. Lett. 2016; 973
• 21 Lu H, Wang L, Yang F, Wu R, Shen W. RSC Adv. 2014; 4: 30447
• 22 Zhang W, Chen G, Wang K, Xia R. Appl. Organomet. Chem. 2019; 33: e4914
• 23 Lv L, Zhu D, Tang J, Qiu Z, Li C.-C, Gao J, Li C.-J. ACS Catal. 2018; 8: 4622
• 24 Zhong S, Chen M, Liu G, Sun C, Liu W. Appl. Organomet. Chem. 2017; 31: e3705
• 25 Kang K, Huang L, Weix DJ. J. Am. Chem. Soc. 2020; 142: 10634
• 26 Ogata T, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 13848
• 27 Gøgsig TM, Lindhardt AT, Dekhane M, Grouleff J, Skrydstrup T. Chem. Eur. J. 2009; 15: 5950
• 28 Kubota Y, Nakada S, Sugi Y. Synlett 1998; 183

For examples of Fe-catalyzed Kumada couplings that are selective for reaction at Cl, see:
• 29a Agata R, Takaya H, Matsuda H, Nakatani N, Takeuchi K, Iwamoto T, Hatakeyama T, Nakamura M. Bull. Chem. Soc. Jpn. 2019; 92: 381
• 29b Wang L, Wei Y.-M, Zhao Y, Duan X.-F. J. Org. Chem. 2019; 84: 5176

For examples of Ru-catalyzed direct arylations that are selective for reaction at Cl, see:
• 30a Ackermann L, Born R, Vicente R. ChemSusChem 2009; 2: 546
• 30b Ackermann L, Diers E, Manvar A. Org. Lett. 2012; 14: 1154
• 31 For an example of an Fe-catalyzed Kumada coupling that is selective for reaction at OTs, see: Chen X, Quan Z.-J, Wang X.-C. Appl. Organomet. Chem. 2015; 29: 296

For selected reviews, see:
• 32a Li B.-J, Yu D.-G, Sun C.-L, Shi Z.-J. Chem. Eur. J. 2011; 17: 1728
• 32b Zhou T, Szostak M. Catal. Sci. Technol. 2020; 10: 5702

For selected reviews, see:
• 33a Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
• 33b Han F.-S. Chem. Soc. Rev. 2013; 42: 5270
• 33c Tobisu M, Chatani N. Top. Curr. Chem. 2016; 374: 41
• 33d Zeng H, Qiu Z, Domínguez-Huerta A, Hearne Z, Chen Z, Li C.-J. ACS Catal. 2017; 7: 510
• 33e Diao H, Shi Z, Liu F. Synlett 2021; in press; DOI DOI: 10.1055/a-1349-3543.
• 34a Zim D, Lando VR, Dupont J, Monteiro AL. Org. Lett. 2001; 3: 3049
• 34b Guan B.-T, Wang Y, Li B.-J, Yu D.-G, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 14468
• 34c Baghbanzadeh M, Pilger C, Kappe CO. J. Org. Chem. 2011; 76: 1507
• 34d Li X.-J, Zhang J.-L, Geng Y, Jin Z. J. Org. Chem. 2013; 78: 5078
• 34e Chen L, Lang H, Fang L, Yu J, Wang L. Eur. J. Org. Chem. 2014; 2014: 6385
• 34f LaBerge NA, Love JA. Eur. J. Org. Chem. 2015; 5546
• 34g Piontek A, Ochędzan-Siodłak W, Bisz E, Szostak M. Adv. Synth. Catal. 2019; 361: 2329
• 35 An aryl chloride is tolerated in the Ni-catalyzed Suzuki coupling of a more reactive fluorosulfonate; see: Hanley PS, Ober MS, Krasovskiy AL, Whiteker GT, Kruper WJ. ACS Catal. 2015; 5: 5041
• 36a Calculations were performed by using Gaussian16 at the CPCM(1,4-dioxane)-MN15L/6-311++G(2d,p)/SDD(Ni)//MN15L/6-31G/6-31+G(Cl, O)/LANL2DZ(Ni) level of theory.
• 37 Hooker LV, Neufeldt SR. Tetrahedron 2018; 74: 6717

For examples of Ni-catalyzed divergent selectivity between activation of C(aryl)-O and C(acyl)-O bonds of aryl esters, where selectivity depends on the ligation state of nickel, see:
• 38a Hong Z, Liang Y, Houk KN. J. Am. Chem. Soc. 2014; 136: 2017
• 39 Tolman CA. Chem. Rev. 1977; 77: 313
• 40 Arjona O, Plumet J. In Encyclopedia of Reagents for Organic Synthesis . Wiley; Hoboken: 2004. DOI: 10.1002/047084289X.rn00394

For evaluation or use of PMe₃ in other types of Ni-catalyzed couplings, see:
• 41a Miller JA, Dankwardt JW, Penney JM. Synthesis 2003; 1643
• 41b Miller JA, Dankwardt JW. Tetrahedron Lett. 2003; 44: 1907
• 41c Dankwardt JW. Angew. Chem. Int. Ed. 2004; 43: 2428
• 41d Yang X, Sun H, Zhang S, Li X. J. Organomet. Chem. 2013; 723: 36
• 41e Tang J, Lv L, Dai X.-J, Li C.-C, Li L, Li C.-J. Chem. Commun. 2018; 54: 1750
• 41f Lv L, Li J, Liu M, Li C.-J. Nat. Commun. 2018; 9: 4739

For the use of PMe₃ as a ligand for Pd-catalyzed cross-couplings, see:
• 42a Widdowson DA, Wilhelm R. Chem. Commun. 1999; 2211
• 42b Widdowson DA, Wilhelm R. J. Chem. Soc., Perkin Trans. 1 2000; 3808
• 42c Miller JA. Tetrahedron Lett. 2001; 42: 6991
• 42d Tang S, Li S.-H, Yan W.-b. Tetrahedron Lett. 2012; 53: 6743
• 42e Balam-Villarreal JA, Sandoval-Chávez CI, Ortega-Jiménez F, Toscano RA, Carreón-Castro MP, López-Cortés JG, Ortega-Alfaro MC. J. Organomet. Chem. 2016; 818: 7
• 43a Christian AH, Müller P, Monfette S. Organometallics 2014; 33: 2134
• 43b Payard P.-A, Perego LA, Ciofini I, Grimaud L. ACS Catal. 2018; 8: 4812
• 44 Interestingly, a bipyridine ligand was recently shown to promote C–O-selective reaction of Ni with a chloroaryl tosylate in the presence of Pd as part of a cross-electrophile coupling; see ref. 25.