Modular Dihydrobenzoazaphosphole Ligands for Suzuki–Miyaura Cross-Coupling

Dedicated to Professor Scott E. Denmark on the occasion of his 65^th birthday

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65^th birthday

Abstract

A new family of dihydrobenzoazaphosphosphole ligands was prepared and shown to enable modification of the phosphine electronic character by variation of the N-substituent. This new family of phosphines was shown to be highly active in the Pd-catalyzed Suzuki–Miyaura cross-coupling reaction with hindered coupling partners.

Key words

dihydrobenzoazaphosphosphole - ligand - N-substituent - palladium - Suzuki–Miyaura cross-coupling

• References

• 1a Seechurn CC. C. J. Kitching MO. Colacot TJ. Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
• 1b Gildner PG. Colacot TJ. Organometallics 2015; 34: 5497
• 1c New Trends in Cross-Coupling: Theory and Applications. Colacot TJ. RSC Publishing; Cambridge: 2015
• 2a Trost BM. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5348
• 2b Farina V. Reeves JT. Senanayake CH. Song JJ. Chem. Rev. 2006; 106: 2734
• 2c Busacca CA. Fandrick DR. Song JJ. Senanayake CH. Adv. Synth. Catal. 2011; 353: 1825
• 2d Torborg C. Beller M. Adv. Synth. Catal. 2009; 351: 3027
• 3a Tolman CA. Chem. Rev. 1977; 77: 313
• 3b Rahman MM. Liu H.-Y. Eriks K. Prock A. Giering WP. Organometallics 1989; 8: 1
• 3c Amatore C. Carre E. Jutand A. M’Barki MA. Organometallics 1995; 14: 1818
• 3d Serron S. Huang J. Nolan SP. Organometallics 1998; 17: 534
• 3e Clavier H. Nolan SP. Chem. Commun. 2010; 46: 841
• 3f Wu K. Doyle AG. Nat. Chem. 2017; 9: 779
• 3g Roschangar F. Colberg J. Dunn PJ. Gallou F. Hayler JD. Koenig SG. Kopach ME. Leahy DK. Mergelsberg I. Tucker JL. Sheldon RA. Senanayake CH. Green Chem. 2017; 19: 281
• 3h Berrisford DJ. Bolm C. Sharpless KB. Angew. Chem., Int. Ed. Engl. 1995; 34: 1059
• 4a Yoon TP. Jacobsen EN. Science 2003; 299: 1691
• 4b Pfaltz A. Drury WJ. III. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5723
• 5a Tang W. Capacci AG. Wei X. Li W. White A. Patel ND. Savoie J. Gao JJ. Rodriguez S. Qu B. Haddad N. Lu BZ. Krishnamurthy D. Yee NK. Senanayake CH. Angew. Chem. Int. Ed. 2010; 49: 5879
• 5b Zhao Q. Li C. Senanayake CH. Tang W. Chem. Eur. J. 2013; 19: 2261
• 5c Qu B. Haddad N. Rodriguez S. Sieber JD. Desrosiers J.-N. Patel ND. Zhang Y. Grinberg N. Lee H. Ma S. Ries UJ. Yee NK. Senanayake CH. J. Org. Chem. 2016; 81: 745
• 5d Patel ND. Rivalti D. Buono FG. Chatterjee A. Qu B. Desrosiers J.-N. Rodriguez S. Sieber JD. Haddad N. Fandrick KR. Lee H. Yee NK. Busacca CA. Senanayake CH. Asian J. Org. Chem. 2017; 6: 1285
• 5e Li G. Wang X.-J. Zhang Y. Tan Z. DeCroos P. Lorenz JC. Wei X. Grinberg N. Yee NK. Senanayake CH. J. Org. Chem. 2017; 82: 5456

Reviews:
• 6a Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
• 6b Kotha S. Lahiri K. Kashinith D. Tetrahedron 2002; 58: 9633
• 6c Jana R. Pathak TP. Sigman MS. Chem. Rev. 2011; 111: 1417
• 7 Roy D. Uozumi Y. Adv. Synth. Catal. 2018; 360: 602

Examples of synthesis of azaphospholes and their applications, see:
• 8a Zhang L. Yu W. Liu C. Xu Y. Duan Z. Mathey F. Organometallics 2015; 34: 5697
• 8b Ghalib M. Jones PG. Lysenko S. Heinicke JW. Organometallics 2014; 33: 804
• 8c Couture A. Deniau E. Grandclaudon P. J. Chem. Soc., Chem. Commun. 1994; 1329
• 9 Zatolochnaya OV. Rodríguez S. Zhang Y. Lao KS. Tcyrulnikov S. Li G. Wang X.-J. Qu B. Biswas S. Mangunuru HP. R. Rivalti D. Sieber JD. Desrosiers J-N. Leung JC. Grinberg N. Lee H. Haddad N. Yee NK. Song JJ. Kozlowski MC. Senanayake CH. Chem. Sci. 2018; 9: 4505
• 10 Sieber JD. Qu B. Rodriguez S. Haddad N. Grinberg N. Lee H. Song JJ. Yee NK. Senanayake CH. J. Org. Chem. 2016; 81: 729

Reviews:
• 11a Surry DS. Buchwald SL. Chem. Sci. 2011; 2: 27
• 11b Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
• 11c Hartwig JF. Acc. Chem. Res. 1998; 31: 852
• 11d Wolfe JP. Wagawa S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998; 31: 805
• 12a Naumann K. Zon B. Mislow K. J. Am. Chem. Soc. 1969; 91: 7012
• 12b Krenske EH. J. Org. Chem. 2012; 77: 3969
• 13a Walker SD. Barder TE. Martinelli JR. Buchwald SL. Angew. Chem. Int. Ed. 2004; 43: 1871
• 13b Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685