TY - JOUR
T1 - 2:1 versus 1:1 Coupling of Alkylacetylenes with Secondary Amines
T2 - Selectivity Switching in 8-Quinolinolato Rhodium Catalysis
AU - Morimoto, Yoshihiko
AU - Hamada, Moe
AU - Takano, Shotaro
AU - Mochizuki, Katsufumi
AU - Kochi, Takuya
AU - Kakiuchi, Fumitoshi
N1 - Funding Information:
F.K. acknowledges financial support, in part, by the Promotion of Science (JSPS) KAKENHI Grant No. JP15H05839 in Middle Molecular Strategy, Japan. Y.M. is also grateful for support by the Research Grant of Keio Leading-edge Laboratory of Science & Technology and Research Grant of Keio Research Development and Sponsored Projects, Faculty of Science & Technology.
Publisher Copyright:
©
PY - 2021/5/21
Y1 - 2021/5/21
N2 - Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products.
AB - Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products.
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U2 - 10.1021/acs.orglett.1c00094
DO - 10.1021/acs.orglett.1c00094
M3 - Article
C2 - 33683910
AN - SCOPUS:85103381849
SN - 1523-7060
VL - 23
SP - 3803
EP - 3808
JO - Organic Letters
JF - Organic Letters
IS - 10
ER -