TY - JOUR
T1 - Catalytic Amide-Base System of TMAF and N(TMS) 3 for Deprotonative Coupling of Benzylic C(sp 3 )-H Bonds with Carbonyls
AU - Shigeno, Masanori
AU - Nakaji, Kunihito
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
PY - 2019/4/19
Y1 - 2019/4/19
N2 - This paper describes that an amide-base generated in situ from tetramethylammonium fluoride (TMAF) and N(TMS) 3 catalyzes the deprotonative coupling of benzylic C(sp 3 )-H bonds with carbonyls to form stilbenes. A variety of methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.
AB - This paper describes that an amide-base generated in situ from tetramethylammonium fluoride (TMAF) and N(TMS) 3 catalyzes the deprotonative coupling of benzylic C(sp 3 )-H bonds with carbonyls to form stilbenes. A variety of methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.
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U2 - 10.1021/acs.orglett.9b00550
DO - 10.1021/acs.orglett.9b00550
M3 - Article
C2 - 30950279
AN - SCOPUS:85064331132
VL - 21
SP - 2588
EP - 2592
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 8
ER -