Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis

Royal Society Open Science

Volumn 3, Issue 5, 2016, Pages

  Arimori, Sadayuki ^a   Matsubara, Okiya ^a   Takada, Masahiro ^a   Shiro, Motoo ^b   Shibata, Norio ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

Carbene; Difluoromethylthiolation; Fluorine; Hypervalent iodonium ylide; Sulfur

Indexed keywords

EID: 84969981849     PISSN: None     EISSN: 20545703     Source Type: Journal    
DOI: 10.1098/rsos.160102     Document Type: Article

References (72)

1. Kirsh P. 2013 Modern fluoroorganic chemistry: synthesis reactivity, applications, 2nd edn. Weinheim, Germany: Wiley-VCH.
2. Ojima I (ed.) 2009 Fluorine in medicinal chemistry and chemical biology. Chichester, UK: Wiley.
3. Bégué JP, Bonnet-Delpon D (eds). 2008 Biioorganic andmedicinal chemistry of fluorine. Hoboken, NJ: Wiley.
4. Purser S, Moore PR, Swallow S, Gouverneur V. 2008 Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 320-330. (doi: 10. 1039/B610213C)
5. Hagman WK. 2008 The many roles for fluorine in medicinal chemistry. J. Med. Chem. 51, 4359-4369. (doi: 10. 1021/jm800219f)
6. Ilardi EA, Vitaku E, Njardarson JT. 2014 Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery. J. Med. Chem. 57, 2832-2842. (doi: 10. 1021/jm401375q)
7. Beno BR, Yeung KS, Bartberger MD, Pennington LD, Meanwell NA. 2015 A survey of the role of non-covalent sulfur interactions in drug design. J. Med. Chem. 58, 4383-4438. (doi: 10. 1021/jm501853m)
8. Phipps RJ, Toste FD. 2013 Chiral anion phase-transfer catalysis applied to the direct enantioselective fluorinative dearomatization of phenols. J. Am. Chem. Soc. 135, 1268-1271. (doi: 10. 1021/ja311798q)
9. Thiehoff C, Holland MC, Daniliuc C, Houk KN, Gilmour R. 2015 Can acyclic conformational control be achieved via a sulfur-fluorine gauche effect? Chem. Sci. 6, 3565-3571. (doi: 10. 1039/C5SC00871A)
10. Fustero S, Simón-Fuentes A, Barrio P, Haufe G. 2015 Olefin metathesis reactions with fluorinated substrates, catalysts and solvents. Chem. Rev. 115, 871-930. (doi: 10. 1021/cr500182a)
11. Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. 2014 Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011). Chem. Rev. 114, 2432-2506. (doi: 10. 1021/cr4002879)
12. Jeschke P. 2004 The unique role of fluorine in the design of active ingredients for modern crop protection. Chem BioChem 5, 570-589. (doi: 10. 1002/ cbic. 200300833)
13. Yale HL. 1959 The trifluoromethyl group in medical chemistry. J. Med. Chem. 1, 121-133. (doi: 10. 1021/jm 50003a001)
14. Liang T, Neumann CN, Ritter T. 2013 Introduction of fluorine and fluorine-containing functional groups. Angew. Chem. Int. Ed. 52, 8214-8264. (doi: 10. 1002/ anie. 201206566) Angew. Chem. 125, 8372-8423. (doi: 10. 1002/ange. 201206566)
15. Hojczyk KN, Feng P, Zhan C, Ngai MY. 2014 Trifluoromethoxylation of arenes: synthesis of ortho-trifluoromethoxylated aniline derivatives by OCF3 migration. Angew. Chem. Int. Ed. 53, 14 559-14 563. (doi: 10. 1002/anie. 201409375) Angew. Chem. 126, 14 787-14 791. (doi: 10. 1002/ ange. 201409375)
16. Toulgoat F, Alazet S, Billard T. 2014 Direct trifluoromethylthiolation reactions: the 'Renaissance' of an old concept. Eur. J. Org. Chem. 2014, 2415-2428. (doi: 10. 1002/ejoc. 201301857)
17. Yang X, Wu T, Phipps R, Phipps J, Toste FD. 2015 Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions. Chem. Rev. 115, 826-870. (doi: 10. 1021/cr500277b)
18. Yin G, Kalvet I, Englert U, Schoenebeck F. 2015 Fundamental studies and development of nickel-catalyzed trifluoromethylthiolation of aryl chlorides: active catalytic species and key roles of ligand and traceless MeCN additive revealed. J. Am. Chem. Soc. 137, 4164-4172. (doi: 10. 1021/jacs. 5b00538)
19. Guo S, Zhang X, Tang P. 2015 Silver-mediated oxidative aliphatic C-H trifluoromethylthiolation. Angew. Chem. Int. Ed. 54, 4065-4069. (doi: 10. 1002/ anie. 201411807)
20. Wu H, Xiao Z, Wu J, Guo Y, Xiao JC, Liu C, Chen QY. 2015 Direct trifluoromethylthiolation of unactivated C(sp3)-H using silver(I) trifluoromethanethiolate and potassium persulfate. Angew. Chem. Int. Ed. 54, 4070-4074. (doi: 10. 1002/anie. 201411953)
21. Weng Z, HeW, Chen C, Lee R, Tan D, Lai Z, Kong D, Yuan Y, Huang KW. 2013 An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides. Angew. Chem. Int. Ed. 52, 1548-1552. (doi: 10. 1002/anie. 201208432) Angew. Chem. 125, 1588-1592. (doi: 10. 1002/ange. 201208432)
22. Xu C, Ma B, Shen Q. 2014 N-Trifluoromethylthiosaccharin: an easily accessible, shelf-stable, broadly applicable trifluoromethylthiolating reagent. Angew. Chem. Int. Ed. 53, 9316-9320. (doi: 10. 1002/anie. 201403983)
23. Shao X, Wang X, Yang T, Lu L, Shen Q. 2013 An electrophilic hypervalent iodine reagent for trifluoromethylthiolation. Angew. Chem. Int. Ed. 52, 3457-3460. (doi: 10. 1002/anie. 201209817) Angew. Chem. 125, 3541-3544. (doi: 10. 1002/ange. 2012 09817)
24. Chen C, Xie Y, Chu L, Wang RW, Zhang X, Qing FL. 2012 Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur. Angew. Chem. Int. Ed. 51, 2492-2495. (doi: 10. 1002/anie. 201108663) Angew. Chem. 2012, 124, 2542-2545. (doi: 10. 1002/anie. 201208432) Angew. Chem. 125, 1588-1592. (doi: 10. 1002/ange. 201108663)
25. Alazet S, Zimmer L, Billard T. 2013 Base-catalyzed electrophilic trifluoromethylthiolation of terminal alkynes. Angew. Chem. Int. Ed. 52, 10 814-10 817. (doi: 10. 1002/anie. 201305179)
26. Jiang L, Qian J, Yi W, Lu G, Cai C, Zhang W. 2015 Direct trifluoromethylthiolation and perfluoroalkylthiolation of C(sp2)-H bonds with CF3SO2Na and RfSO2Na. Angew. Chem. Int. Ed. 54, 14 965-14 969. (doi: 10. 1002/anie. 201508495)
27. Tlili A, Billard T. 2013 Formation of C-SCF3 bonds through direct trifluoromethylthiolation. Angew. Chem. Int. Ed. 52, 6818-6819. (doi: 10. 1002/anie. 201301438)
28. Baert F, Colomb J, Billard T. 2012 Electrophilic trifluoromethanesulfanylation of organometallic species with trifluoromethanesulfanamides. Angew. Chem. Int. Ed. 51, 10 382-10 385. (doi: 10. 1002/anie. 201205156)
29. Ferry A, Billard T, Langlois BR, Bacqué E. 2009 Trifluoromethanesulfanylamides as easy-to-handle equivalents of the trifluoromethanesulfanyl cation (CF3S+): reaction with alkenes and alkynes. Angew. Chem. Int. Ed. 48, 8551-8555. (doi: 10. 1002/anie. 200903387)
30. Pluta R, Nikolaienko P, Rueping M. 2014 Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide. Angew. Chem. Int. Ed. 53, 1650-1653. (doi: 10. 1002/ anie. 201307484)
31. Hu F, Shao X, Zhu D, Lu L, Shen Q. 2014 Silver-catalyzed decarboxylative trifluoromethylthiolation of aliphatic carboxylic acids in aqueous emulsion. Angew. Chem. Int. Ed. 53, 6105-6109. (doi: 10. 1002/anie. 201402573)
32. Zhang CP, Vicic DA. 2012 Nickel-catalyzed synthesis of aryl trifluoromethyl sulfides at room temperature. J. Am. Chem. Soc. 134, 183-185. (doi: 10. 1021/ja210364r)
33. Chen C, Chu L, Qing FL. 2012 Metal-free oxidative trifluoromethylthiolation of terminal alkynes with CF3SiMe3 and elemental sulfur. J. Am. Chem. Soc. 134, 12 454-12 457. (doi: 10. 1021/ja305801m)
34. Liu JB, Xu XH, Chen ZH, Qing FL. 2015 Direct dehydroxytrifluoromethylthiolation of alcohols using silver(I) trifluoromethanethiolate and tetra-n-butylammonium iodide. Angew. Chem. Int. Ed. 54, 897-900. (doi: 10. 1002/anie. 201409983)
35. Yang T, Lu L, Shen Q. 2015 Iron-mediated Markovnikov-selective hydro-trifluoromethylthiolation of unactivated alkenes. Chem. Commun. 51, 5479-5481. (doi: 10. 1039/C4CC08655D)
36. Adams DJ, Goddard A, Clark JH, Macquarrie DJ. 2000 Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides. Chem. Commun. 987-988. (doi: 10. 1039/ B002560G)
37. Li M, Guo J, Xue XS, Cheng JP. 2016 Quantitative scale for the trifluoromethylthio cation-donating ability of electrophilic trifluoromethylthiolating reagents. Org. Lett. 18, 264-267. (doi: 10. 1021/acs. orglett. 5b03433)
38. Teverovsky G, Surry DS, Buchwald S. 2011 Pdcatalyzed synthesis of Ar-SCF3 compounds under mild conditions. Angew. Chem. Int. Ed. 50, 7312-7314. (doi: 10. 1002/anie. 201102543) Angew. Chem. 123, 7450-7452. (doi: 10. 1002/ange. 201102543)
39. Leroux F, Jeschke P, Schlosser M. 2005 α-Fluorinated ethers, thioethers, and amines: anomerically biased species. Chem. Rev. 105, 827-856. (doi: 10. 1021/cr040075b)
40. Xu XH, Matsuzaki K, Shibata N. 2015 Synthetic methods for compounds having CF3-S units on carbon by trifluoromethylation, trifluoromethylthiolation, triflylation, and related reactions. Chem. Rev. 115, 731-764. (doi: 10. 1021/cr500193b)
41. Ni C, HuM, Hu J. 2015 Good partnership between sulfur and fluorine: sulfur-based fluorination and fluoroalkylation reagents for organic synthesis. Chem. Rev. 115, 765-825. (doi: 10. 1021/cr5002386)
42. Li Y, Hu J. 2005 Facile synthesis of chiralα-difluoromethyl amines from N-(tert-butylsulfinyl) aldimines. Angew. Chem. Int. Ed. 44, 5882-5886. (doi: 10. 1002/anie. 200501769) Angew. Chem. 117, 6032-6036. (doi: 10. 1002/ange. 200501769)
43. Brahms DLS, Dailey WP. 1996 Fluorinated carbenes. Chem. Rev. 96, 1585-1632. (doi: 10. 1021/cr941141k)
44. Langlois BR. 1988 Improvement of the synthesis of aryl difluoromethyl ethers and thioethers by using a solid-liquid phase-transfer technique. J. Fluorine Chem. 41, 247-261.
45. Hine J, Porter JJ. 1960 Methylenes as intermediates in polar reactions. XXI. A sulfur-containing methylene. J. Am. Chem. Soc. 82, 6118-6120. (doi: 10. 1021/ja01508a036)
46. Deprez P, Vevert JP. 1996 Synthesis of difluoromethylthio imidazole from methylthio imidazole. J. Fluorine Chem. 80, 159-162. (doi: 10. 1016/S0022-1139(96)03497-5)
47. Zafrani Y, Sod-Moriah G, Segall Y. 2009 Diethyl bromodifluoromethylphosphonate: a highly efficient and environmentally benign difluorocarbene precursor. Tetrahedron 65, 5278-5283. (doi: 10. 1016/j. tet. 2009. 04. 082)
48. Zhang W, Wang F, Hu J. 2009 N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: a new difluoromethylation reagent for S-, N-, and C-nucleophiles. Org. Lett. 11, 2109-2112. (doi: 10. 1021/ol900567c)
49. Li L, Wang F, Ni C, Hu J. 2013 Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF2Br. Angew. Chem. Int. Ed. 52, 12 390-12 394. (doi: 10. 1002/anie. 201306703)
50. Metha VP, Greaney MF. 2013 S-, N-, and Se-Difluoromethylation using sodium chlorodifluoroacetate. Org. Lett. 15, 5036-5039. (doi: 10. 1021/ol402370f)
51. Fuchibe K, Bando M, Takayama R, Ichikawa J. 2015 Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds. J. Fluorine Chem. 171, 133-138. (doi: 10. 1016/j. jfluchem. 2014. 08. 013)
52. Chen QY, Wu SW. 1989 A simple convenient method for preparation of difluoromethyl ethers using fluorosulfonyldifluoroacetic acid as a difluorocarbene precursor. J. Fluorine Chem. 44, 433-440. (doi: 10. 1016/S0022-1139(00)82808-0)
53. Deng XY, Lin JH, Zheng J, Xiao JC. 2015 Difluoromethylation and gem-difluorocyclopropenation with difluorocarbene generated by decarboxylation. Chem. Commun. 51, 8805-8808. (doi: 10. 1039/C5CC02736E)
54. Fujiwara Y, Dixon JA, Rodriguez RA, Baxter RD, Dixon DD, Collins MR, Blackmond DG, Baran PS. 2012 A new reagent for direct difluoromethylation. J. Am. Chem. Soc. 134, 1494-1497. (doi: 10. 1021/ja211422g)
55. Surya Prakash GK, Zhang Z, Wang F, Ni C, Olah GA. 2011 N, N-Dimethyl-S-difluoromethyl-S-phenylsulfoximinium tetrafluoroborate: a versatile electrophilic difluoromethylating reagent. J. Fluorine Chem. 132, 792-798. (doi: 10. 1016/j. jfluchem. 2011. 04. 023)
56. Zhang W, Zhu JM, Hu J. 2008 Electrophilic (phenylsulfonyl)difluoromethylation of thiols with a hypervalent iodine(III)-CF2SO2Ph reagent. Tetrahedron Lett. 49, 5006-5008. (doi: 10. 1016/j. tetlet. 2008. 06. 064)
57. Bayarmagnai B, Matheis C, Jouvin K, Goosen LJ. 2015 Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ. Angew. Chem. Int. Ed. 54, 5753-5756. (doi: 10. 1002/anie. 201500899)
58. Jouvin K, Mathesis C, Goossen LJ. 2015 Synthesis of aryl tri-and difluoromethyl thioethers via a C-H-thiocyanation/fluoroalkylation cascade. Chem. Eur. J. 21, 14 324-14 327. (doi: 10. 1002/chem. 201502914)
59. Fier PS, Hartwig JF. 2013 Synthesis of difluoromethyl ethers with difluoromethyltriflate. Angew. Chem. Int. Ed. 52, 2092-2095. (doi: 10. 1002/anie. 2012 09250) Angew. Chem. 125, 2146-2149. (doi: 10. 1002/ ange. 201209250)
60. Wu J, Gu Y, Leng X, Shen Q. 2015 Copper-promoted Sandmeyer difluoromethylthiolation of aryl and heteroaryl diazonium salts. Angew. Chem. Int. Ed. 54, 7648-7652. (doi: 10. 1002/anie. 201502113)
61. Zhu D, Gu Y, Lu L, Shen Q. 2015 N-Difluoromethylthiophthalimide: a shelf-stable, electrophilic reagent for difluoromethylthiolation. J. Am. Chem. Soc. 137, 10 547-10 553. (doi: 10. 1021/jacs. 5b03170)
62. Yang YD, Azuma A, Tokunaga E, Yamamoto M, Shiro M, Shibata N. 2013 Trifluoromethanesulfonyl hypervalent iodonium ylide for copper-catalyzed trifluoromethylthiolation of enamines, indoles, and β-keto esters. J. Am. Chem. Soc. 135, 8782-8785. (doi: 10. 1021/ja402455f)
63. Huang Z, Yang YD, Tokunaga E, Shibata N. 2015 copper-catalyzed regioselective trifluoromethylthiolation of pyrroles by trifluoromethanesulfonyl hypervalent iodonium ylide. Org. Lett. 17, 1094-1097. (doi: 10. 1021/ ol503616y)
64. Arimori S, Takada M, Shibata N. 2015 Trifluoromethylthiolation of allylsilanes and silyl enol ethers with trifluoromethanesulfonyl hypervalent iodonium ylide under copper catalysis. Org. Lett. 17, 1063-1065. (doi: 10. 1021/acs. orglett. 5b00057)
65. Arimori S, Takada M, Shibata N. 2015 Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis. Dalton Trans. 44, 19 456-19 459. (doi: 10. 1039/C5DT02214B)
66. He Z, Tan P, Ni C, Hu J. 2015 Fluoroalkylative aryl migration of conjugated N-arylsulfonylated amides using easily accessible sodium di-and monofluoroalkanesulfinates. Org. Lett. 17, 1838-1841. (doi: 10. 1021/acs. orglett. 5b00308)
67. Kice JL, Kasperek GJ, Patterson D. 1969 Relative nucleophilicity of some common nucleophiles toward sulfonyl sulfur. Nucleophile-catalyzed hydrolysis and other nucleophilic substitution reactions of arylα-disulfones. J. Am. Chem. Soc. 91, 5516-5522. (doi: 10. 1021/ja 01048a020)
68. Soloshonok VA, Ueki H, Yasumoto M, Mekala S, Hirschi JS, Singleton DA. 2007 Phenomenon of optical self-purification of chiral non-racemic compounds. J. Am. Chem. Soc. 129, 12 112-12 113. (doi: 10. 1021/ja065603a)
69. Soloshonok VA. 2006 remarkable amplification of the self-disproportionation of enantiomers on achiral-phase chromatography columns. Angew. Chem. Int. Ed. 45, 766-769. (doi: 10. 1002/anie. 200503373)
70. O'Hagan D. 2012 Organofluorine chemistry: synthesis and conformation of vicinal fluoromethylene motifs. J. Org. Chem. 77, 3689-3699. (doi: 10. 1021/jo300044q)
71. Buissonneaud DY, Mourik TV, O'Hagan D. 2010 A DFT study on the origin of the fluorine gauche effect in substituted fluoroethanes. Tetrahedron 66, 2196-2202. (doi: 10. 1016/j. tet. 2010. 01. 049)
72. Tavasli M, O'Hagan D, Pearson C, Petty MC. 2002 The fluorine gauche effect. Langmuir isotherms report the relative conformational stability of (±)-erythro-and (±)-threo-9, 10-difluorostearic acids. Chem. Commun. 1226-1227. (doi: 10. 1039/ B202891C)