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 - 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 -