Abstract
Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond.
Graphic abstract
Similar content being viewed by others
References
Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem. Rev. 102:1359
Corbet J, Mignani G (2006) Chem. Rev. 106:2651
Negishi E (2007) Bull. Chem. Soc. Jpn. 80:233
Ahrens T, Kohlmann J, Ahrens M, Braun T (2015) Chem. Rev. 115:931
Böhm VPW, Gstöttmayr CWK, Weskamp T, Herrmann WA (2001) Angew. Chem. Int. Ed. 40:3387
Terao J, Ikumi A, Kuniyasu H, Kambe N (2003) J. Am. Chem. Soc. 125:5646
Ackermann L, Born R, Spatz JH, Meyer D (2005) Angew. Chem. Int. Ed. 44:7216
Yoshikai N, Mashima H, Nakamura E (2005) J. Am. Chem. Soc. 127:17978
Kim YM, Yu S (2003) J. Am. Chem. Soc. 125:1696
Widdowson DA, Wilhelm R (2003) Chem. Commun. 5:578
Schaub T, Backes M, Radius U (2006) J. Am. Chem. Soc. 128:15964
Gallon BJ, Kojima RW, Kaner RB, Diaconescu PL (2007) Angew. Chem. Int. Ed. 46:7251
Tobisu M, Xu T, Shimasaki T, Chatani N (2011) J. Am. Chem. Soc. 133:19505
Terao J, Todo H, Watanabe H, Ikumi A, Kambe N (2004) Angew. Chem. Int. Ed. 43:6180
Takachi M, Kita Y, Tobisu M, Fukumoto Y, Chatani N (2010) Angew. Chem. Int. Ed. 49:8717
Ohashi M, Kambara T, Hatanaka T, Saijo H, Doi R, Ogoshi S (2011) J. Am. Chem. Soc. 133:3256
Duthaler RO, Hafner A (1998). In: Beller M, Bolm C (eds) Transition Metals for Organic Synthesis, vol 1. Wiley-VCH, Weinheim, p 447
Sato F, Urabe H, Okamoto S (2000) Chem. Rev. 100:2835
Han JW, Tokunaga N, Hayashi T (2002) Synlett 6:871
Dastbaravardeh N, Knochel P (2007) Synlett 13:2077
Yang T, Zhou SL, Chang FS, Chen CR, Gau HM (2009) Organometallics 28:5715
Chen CR, Zhou SL, Biradar DB, Gau HM (2010) Adv. Syn. Catal. 352:1718
Chang ST, Li QH, Chiang RT, Gau HM (2012) Tetrahedron 68:3956
Varenikov A, Gandelman M (2019) J. Am. Chem. Soc. 141:10994
Varenikov A, Shapiro E, Gandelman M (2020) Org. Lett. 22:9386
Lee HW, Lam FL, So CM, Lau CP, Chan ASC, Kwong FY (2009) Angew. Chem. Int. Ed. 48:7436
Lee HW, So CM, Yuen OY, Wong WT, Kwong FY (2020) Org. Chem. Front. 7:926
Ohashi M, Doi R, Ogoshi S (2014) Chem. Eur. J. 20:2040
Shirakawa E, Tamakuni F, Kusano E, Uchiyama N, Konagaya W, Watabe R, Hayashi T (2014) Angew. Chem. Int. Ed. 53:521
Duan H, Meng L, Bao D, Zhang H, Li Y, Lei A (2010) Angew. Chem. Int. Ed. 49:6387
Kumar S, Kumar GS, Kumar RA, Reddy NV, Reddy KR (2013) Eur. J. Org. Chem. 7:1218
O'Brien JP, Schuetz RD, Taft DD, Shea JL, Mork HM (1963) J. Org. Chem. 28:1420
Greulich SW, Daniliuc CG, Studer A (2015) Org. Lett. 17:254
Konstantinović J, Mikloš T, Burojević J, Djaković OD, Srbljanović J, Štajner T, Verbić T, Zlatović M, Machado M, Albuquerque IS, Prudêncio M, Sciotti RJ, Pecic S, D’Alessandro S, Taramelli D, Šolaja BA (2016) J. Med. Chem. 59:264
Bedford RB, Brenner PB, Carter E, Clifton J, Cogswell PM, Gower NJ, Haddow MF, Harvey JN, Kehl JA, Murphy DM, Neeve EC, Neidig ML, Nunn J, Snyder BER, Taylor J (2014) Organometallics 33:5767
Li CJ (2020) Russ. J. Gen. Chem. 90:725
Ueda Y, Iwai T, Sawamura M (2018) Chem. Commun. 54:1718
Li PB, Lü B, Fu CL, Ma SM (2013) Adv. Syn. Cata. 355:1255
He X-Y (2021) J. Chem. Res. https://doi.org/10.1177/1747519821994533
Krasovskiy A, Knochel P (2004) Angew. Chem. Int. Ed. 43:3333
Krasovskiy A, Knochel P (2006) Synthesis 5:890
Acknowledgements
The author gratefully acknowledge the financial support from Hebei Chemical & Pharmaceutical College and the Higher Education Scientific Research Project of Hebei Province (2020) (SQ201044). The author is thankful to Hebei University of Science & Technology for 13C NMR, 1H NMR, HRMS (ESI) measurement.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
He, XY. A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents. Monatsh Chem 152, 823–832 (2021). https://doi.org/10.1007/s00706-021-02796-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-021-02796-6