Diastereoselective Pd-Catalyzed Domino Heck/Arylborylation Sequence Forming Borylated Chromans

Abstract

A diastereoselective palladium-catalyzed domino Heck/arylborylation of aryl iodides yielding an alkylboronate containing a chroman is reported. The generated alkylpalladium(II) intermediate is intercepted with bis(pinacolato)diboron (B₂pin₂) in good yield as a single diastereomer.

Key words

palladium - Heck reaction - alkylboronate - diastereoselective - chroman - benzopyran

• References

• 1 Boronic Acids: Prepartion and Applications in Organic Synthesis and Medicine. 2nd ed., Hall DG. Wiley-VCH; Weinheim: 2011

For selected reviews, see:
• 2a Ishiyama T, Miyaura N. Chem. Rec. 2004; 3: 271
• 2b Chow WK, Yuen OY, Choy PY, So CM, Lau CP, Wing TW, Kwong FK. RSC Adv. 2013; 3: 12518 ; and references therein

For selected examples:
• 3a Brown HC, Cole TE. Organometallics 1983; 2: 1316
• 3b Li W, Nelson DP, Jenson MS, Hoerrner RS, Cai D, Larsen RD, Reider PJ. J. Org. Chem. 2002; 67: 5394
• 3c Huang S, Petersen TB, Lipshutz BH. J. Am. Chem. Soc. 2010; 132: 14021
• 3d Demory E, Blandin V, Einhorn J, Chavant PY. Org. Process Res. Dev. 2011; 15: 710
• 3e Leerman T, Leroux FR, Colobert F. Org. Lett. 2011; 13: 4479

For selected reviews and examples, see:
• 4a Hartwig JF. J. Am. Chem. Soc. 2016; 138: 2
• 4b Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
• 4c Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 134

For reviews on the Pd-catalyzed intramolecular Heck reaction, see:
• 5a Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644
• 5b Shibasaki M, Vogl EM, Ohshima T. Adv. Synth. Catal. 2004; 346: 1533

For reviews on total syntheses using the Pd-catalyzed intramolecular Heck reaction, see:
• 6a Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
• 6b Dounay AB, Overman LE. Chem. Rev. 2003; 103: 2945
• 7 Grigg R, Sridharan V. J. Organomet. Chem. 1999; 576: 65
• 8 For a review, see: Vlaar T, Ruijter E, Orru RV. A. Adv. Synth. Catal. 2011; 353: 809 ; and references therein

For recent selected examples:
• 9a Liu Z, Xia Y, Zhou S, Wang L, Zhang Y, Wang J. Org. Lett. 2013; 15: 5032
• 9b Liu X, Ma X, Huang Y, Gu Z. Org. Lett. 2013; 15: 4814
• 9c Yoon H, Petrone DA, Lautens M. Org. Lett. 2014; 16: 6420
• 9d Zhou M.-B, Huang X.-C, Liu Y.-Y, Song R.-J, Li J.-H. Chem. Eur. J. 2014; 20: 1843
• 9e Petrone DA, Yen A, Zeidan N, Lautens M. Org. Lett. 2015; 17: 4838
• 9f Sharma UK, Sharma N, Kumar Y, Singh BK, Van der Eycken EV. Chem. Eur. J. 2016; 22: 481

For selected examples:
• 10a Marco-Martínez J, López-Carrillo V, Buñuel E, Simancas R, Cárdenas DJ. J. Am. Chem. Soc. 2007; 129: 1874
• 10b Marco-Martínez J, Buñuel E, Muñoz-Rodríguez R, Cárdenas DJ. Org. Lett. 2008; 10: 3619
• 10c Pardo-Rodríguez V, Marco-Martínez J, Buñuel E, Cárdenas DJ. Org. Lett. 2009; 11: 4548
• 10d Pardo-Rodríguez V, Buñuel E, Collado-Sanz D, Cárdenas DJ. Chem. Commun. 2012; 48: 10517
• 10e Martos-Redruejo A, López-Durán R, Buñuel E, Cárdenas DJ. Chem. Commun. 2014; 50: 10094
• 10f Camelio AM, Barton T, Guo F, Shaw T, Siegel D. Org. Lett. 2011; 13: 1517
• 10g Persson AK. Å, Jiang T, Johnson MT, Bäckvall J.-E. Angew. Chem. Int. Ed. 2011; 50: 6155
• 10h Deng Y, Bartholomeyzik T, Bäckvall J.-E. Angew. Chem. Int. Ed. 2013; 52: 6283
• 10i Jiang T, Bartholomeyzik T, Mazuela J, Willersinn J, Bäckvall J.-E. Angew. Chem. Int. Ed. 2015; 54: 6024
• 11 Vacchini DD, Butani HH, Sharma N, Bhoya UC, Shah AK, Van der Eycken EV. Chem. Commun. 2015; 51: 14862
• 12 Billingsley KL, Barder TE, Buchwald SL. Angew. Chem. Int. Ed. 2007; 46: 5359
• 13 Wilson JE. Tetrahedron Lett. 2012; 53: 2308
• 14 Petrone DA, Malik HA, Clemenceau A, Lautens M. Org. Lett. 2012; 14: 4806
• 15 Sumimoto M, Iwane N, Takahama T, Sakaki S. J. Am. Chem. Soc. 2004; 126: 10457
• 16 Rossi SA, Shimkin KW, Xu Q, Mori-Quiroz LM, Watson DA. Org. Lett. 2013; 15: 2314
• 17 Morgan JB, Morken JP. J. Am. Chem. Soc. 2004; 126: 15338
• 18 Dreher SD, Lim S.-E, Sandrock DL, Molander GA. J. Org. Chem. 2009; 74: 3626
• 19 Brenstrum T, Gerristma DA, Adjabeng GM, Frampton CS, Britten J, Robertson AJ, McNulty J, Capretta A. J. Org. Chem. 2004; 69: 7635