TY - JOUR
T1 - Less Is More
T2 - N(BOH)2 Configuration Exhibits Higher Reactivity than the B3NO2 Heterocycle in Catalytic Dehydrative Amide Formation
AU - Opie, Christopher R.
AU - Noda, Hidetoshi
AU - Shibasaki, Masakatsu
AU - Kumagai, Naoya
N1 - Funding Information:
This work was supported by KAKENHI (Nos. 20K15292 and 20H02746) from JSPS. Dr. Ryuichi Sawa, Yumiko Kubota, Dr. Kiyoko Iijima, and Dr. Shinya Adachi at the Institute of Microbial Chemistry are gratefully acknowledged for technical assistance in NMR and MS analyses.
Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/2/3
Y1 - 2023/2/3
N2 - Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.
AB - Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.
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U2 - 10.1021/acs.orglett.2c04382
DO - 10.1021/acs.orglett.2c04382
M3 - Article
C2 - 36662124
AN - SCOPUS:85146909812
SN - 1523-7060
VL - 25
SP - 694
EP - 697
JO - Organic Letters
JF - Organic Letters
IS - 4
ER -