Alkyne 1,1-Hydroboration to a Reactive Frustrated P/B-H Lewis Pair.
boron
frustrated Lewis pairs (FLPs)
phosphorus
rearrangement
ylide
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
15 Mar 2021
15 Mar 2021
Historique:
received:
30
10
2020
pubmed:
12
12
2020
medline:
12
12
2020
entrez:
11
12
2020
Statut:
ppublish
Résumé
The Mes
Identifiants
pubmed: 33306863
doi: 10.1002/anie.202014562
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6757-6763Subventions
Organisme : Deutsche Forschungsgemeinschaft
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840;
H. C. Brown, C. G. Scouten, R. Liotta, J. Am. Chem. Soc. 1979, 101, 96-99.
T. Ohmura, Y. Yamamoto, N. Miyaura, J. Am. Chem. Soc. 2000, 122, 4990-4991;
J. V. Obligacion, J. M. Neely, A. N. Yazdani, I. Pappas, P. J. Chirik, J. Am. Chem. Soc. 2015, 137, 5855-5858;
N. Gorgas, L. G. Alves, B. Stöger, A. M. Martins, L. F. Veiros, K. Kircher, J. Am. Chem. Soc. 2017, 139, 8130-8133.
B. Wrackmeyer, C. Bihlmayer, J. Chem. Soc. Chem. Commun. 1981, 1093-1094;
R. L. Ernest, W. Quinatana, R. Rosen, P. J. Carroll, L. G. Sneddon, Organometallics 1987, 6, 80-88;
P. Paetzold, E. Leuschner, Z. Anorg. Allg. Chem. 2002, 628, 658-660;
Q. Feng, H. Wu, X. Li, L. Song, L. W. Chung, Y.-D. Wu, J. Sun, J. Am. Chem. Soc. 2020, 142, 13867-13877.
A. Ueno, J. Yu, X. Tao, C. G. Daniliuc, G. Kehr, G. Erker, Organometallics 2018, 37, 2665-2668, and references therein.
B. Wrackmeyer, Coord. Chem. Rev. 1995, 145, 125-156;
B. Wrackmeyer, E. Khan, Eur. J. Inorg. Chem. 2016, 300-312.
G. Kehr, G. Erker, Chem. Commun. 2012, 48, 1839-1850;
G. Kehr, G. Erker, Chem. Sci. 2016, 7, 56-65.
R. Köster, G. Seidel, B. Wrackmeyer, Chem. Ber. 1989, 122, 1825-1850;
B. Wrackmeyer, S. Kundler, R. Boese, Chem. Ber. 1993, 126, 1361-1370;
C. Chen, G. Kehr, R. Fröhlich, G. Erker, J. Am. Chem. Soc. 2010, 132, 13594-13595;
F. A. Tsao, D. W. Stephan, Dalton Trans. 2015, 44, 71-74;
J. R. Lawson, V. Fasano, J. Cid, I. Vitorica-Yrezabal, M. J. Ingleson, Dalton Trans. 2016, 45, 6060-6070;
K. Škoch, C. Pauly, C. G. Daniliuc, K. Bergander, G. Kehr, G. Erker, Dalton Trans. 2019, 48, 4837-4845;
O. Tok, K. Lang, A. Růžička, J. Cvačka, Angew. Chem. Int. Ed. 2019, 58, 1654-1658;
Angew. Chem. 2019, 131, 1668-1672.
D. J. Parks, R. E. von Spence, W. E. Piers, Angew. Chem. Int. Ed. Engl. 1995, 34, 809-811;
Angew. Chem. 1995, 107, 895-897;
D. J. Parks, W. E. Piers, G. P. A. Yap, Organometallics 1998, 17, 5492-5503;
A. Schnurr, K. Samigullin, J. M. Breunig, M. Bolte, H.-W. Lerner, M. Wagner, Organometallics 2011, 30, 2838-2843;
E. A. Patrick, W. E. Piers, Chem. Commun. 2020, 56, 841-853.
D. W. Stephan, G. Erker, Angew. Chem. Int. Ed. 2015, 54, 6400-6441;
Angew. Chem. 2015, 127, 6498-6541;
D. W. Stephan, Science 2016, 354, aaf7229;
G. Kehr, G. Erker, Chem. Rec. 2017, 17, 803-815.
J. Li, C. G. Daniliuc, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2019, 58, 6737-6741;
Angew. Chem. 2019, 131, 6809-6813;
see also: J. Li, C. G. Daniliuc, C. Mück-Lichtenfeld, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2019, 58, 15377-15380;
Angew. Chem. 2019, 131, 15521-15524;
J. Li, C. Mück-Lichtenfeld, C. G. Daniliuc, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2020, 59, 12477-12483;
Angew. Chem. 2020, 132, 12577-12583;
J. Li, C. G. Daniliuc, K. K. Kartha, G. Fernández, G. Kehr, G. Erker, J. Am. Chem. Soc. 2021, 143, doi: 10.1021/jacs.0c12236.
See for comparison:
G. C. Welch, R. R. San Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126;
P. Spies, G. Erker, G. Kehr, R. Fröhlich, S. Grimme, D. W. Stephan, Chem. Commun. 2007, 5072-5074.
M. W. Rathke, H. C. Brown, J. Am. Chem. Soc. 1966, 88, 2606-2607.
A. B. Burg, H. I. Schlesinger, J. Am. Chem. Soc. 1937, 59, 780-787.
M. Sajid, L.-M. Elmer, C. Rosorius, C. G. Daniliuc, S. Grimme, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2013, 52, 2243-2246;
Angew. Chem. 2013, 125, 2299-2302.
M. Sajid, G. Kehr, C. G. Daniliuc, G. Erker, Angew. Chem. Int. Ed. 2014, 53, 1118-1121;
Angew. Chem. 2014, 126, 1136-1139;
L. Wang, S. Dong, C. G. Daniliuc, L. Liu, S. Grimme, R. Knitsch, H. Eckert, M. D. Hansen, G. Kehr, G. Erker, Chem. Sci. 2018, 9, 1544-1550.
A. Berkefeld, W. A. Piers, M. Parvez, L. Castro, L. Maron, O. Eisenstein, J. Am. Chem. Soc. 2012, 134, 10843-10851;
R. Dobrovetsky, D. W. Stephan, J. Am. Chem. Soc. 2013, 135, 4974-4977.
M. A. Dureen, D. W. Stephan, J. Am. Chem. Soc. 2010, 132, 13559-13568;
M. Sajid, A. Lawzer, W. Dong, C. Rosorius, W. Sander, B. Schirmer, S. Grimme, C. G. Daniliuc, G. Kehr, G. Erker, J. Am. Chem. Soc. 2013, 135, 18567-18574;
O. Ekkert, G. G. Miera, T. Wiegand, H. Eckert, B. Schirmer, P. L. Petersen, C. G. Daniliuc, R. Fröhlich, S. Grimme, G. Kehr, G. Erker, Chem. Sci. 2013, 4, 2657-2664;
A. R. Cabrera, R. S. Rojas, M. Valderarama, P. Plüss, H. Berke, C. G. Daniliuc, G. Kehr, G. Erker, Dalton Trans. 2015, 44, 19606-19614.
G. Schmid, J. Reschke, R. Boese, Chem. Ber. 1994, 127, 1891-1894;
S.-Y. Liu, I. D. Hills, G. C. Fu, Organometallics 2002, 21, 4323-4325;
X. Fang, J. Assoud, Organometallics 2008, 27, 2408-2410;
A. J. Ashe III, Organometallics 2009, 28, 4236-4248;
L. Xie, J. Zhang, C. Cui, Chem. Eur. J. 2014, 20, 9500-9503.
G.-Q. Chen, G. Kehr, C. Mück-Lichtenfeld, C. G. Daniliuc, G. Erker, J. Am. Chem. Soc. 2016, 138, 8554-8559;
J. Li, C. G. Daniliuc, G. Kehr, G. Erker, Eur. J. Inorg. Chem. 2020, 1096-1100.
J. Gasnot, C. Botella, S. Comesse, S. Lakhdar, C. Alayrac, A.-C. Gaumont, V. Dalla, C. Taillier, Angew. Chem. Int. Ed. 2020, 59, 11769-11773;
Angew. Chem. 2020, 132, 11867-11871.
R. T. Boeré, R. T. Oakley, R. W. Reed, J. Organomet. Chem. 1987, 331, 161-167;
M. L. Cole, P. C. Junk, Dalton Trans. 2003, 2109-2111;
A. F. Maddox, K. A. Erickson, J. M. Tanski, R. Waterman, Chem. Commun. 2011, 47, 11769-11771.
S. Döring, G. Erker, R. Fröhlich, O. Meyer, K. Bergander, Organometallics 1998, 17, 2183-2187.
A. Ramos, A. Antiñolo, F. Carrillo-Hermosilla, R. Fernández-Galán, A. Rodriguez-Diéguez, D. García-Vivó, Chem. Commun. 2018, 54, 4700-4703.
M. A. Dureen, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 8396-8397.
M. A. Kropp, G. B. Schuster, J. Am. Chem. Soc. 1989, 111, 2316-2317;
X. Zhao, T. M. Gilbert, D. W. Stephan, Chem. Eur. J. 2010, 16, 10304-10308;
J. Yu, G. Kehr, C. G. Daniliuc, C. Bannwarth, S. Grimme, G. Erker, Org. Biomol. Chem. 2015, 13, 5783-5792.
O. Ekkert, G. Kehr, R. Fröhlich, G. Erker, J. Am. Chem. Soc. 2011, 133, 4610-4616.