Catalytic Amide-Base System of TMAF and N(TMS)                         3                          for Deprotonative Coupling of Benzylic C(sp                         3                         )-H Bonds with Carbonyls

Masanori Shigeno; Kunihito Nakaji; Kanako Nozawa-Kumada; Yoshinori Kondo

doi:10.1021/acs.orglett.9b00550

Catalytic Amide-Base System of TMAF and N(TMS) ₃ for Deprotonative Coupling of Benzylic C(sp ³ )-H Bonds with Carbonyls

Masanori Shigeno, Kunihito Nakaji, Kanako Nozawa-Kumada, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2588-2592
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.9b00550
Publication status	Published - 2019 Apr 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Shigeno, M., Nakaji, K., Nozawa-Kumada, K., & Kondo, Y. (2019). Catalytic Amide-Base System of TMAF and N(TMS) ₃ for Deprotonative Coupling of Benzylic C(sp ³ )-H Bonds with Carbonyls Organic letters, 21(8), 2588-2592. https://doi.org/10.1021/acs.orglett.9b00550

Catalytic Amide-Base System of TMAF and N(TMS) ₃ for Deprotonative Coupling of Benzylic C(sp ³ )-H Bonds with Carbonyls . / Shigeno, Masanori; Nakaji, Kunihito; Nozawa-Kumada, Kanako ; Kondo, Yoshinori.

In: Organic letters, Vol. 21, No. 8, 19.04.2019, p. 2588-2592.

Research output: Contribution to journal › Article › peer-review

Shigeno, M, Nakaji, K, Nozawa-Kumada, K & Kondo, Y 2019, ' Catalytic Amide-Base System of TMAF and N(TMS) ₃ for Deprotonative Coupling of Benzylic C(sp ³ )-H Bonds with Carbonyls ', Organic letters, vol. 21, no. 8, pp. 2588-2592. https://doi.org/10.1021/acs.orglett.9b00550

Shigeno M, Nakaji K, Nozawa-Kumada K , Kondo Y. Catalytic Amide-Base System of TMAF and N(TMS) ₃ for Deprotonative Coupling of Benzylic C(sp ³ )-H Bonds with Carbonyls Organic letters. 2019 Apr 19;21(8):2588-2592. https://doi.org/10.1021/acs.orglett.9b00550

Shigeno, Masanori ; Nakaji, Kunihito ; Nozawa-Kumada, Kanako ; Kondo, Yoshinori. / Catalytic Amide-Base System of TMAF and N(TMS) ₃ for Deprotonative Coupling of Benzylic C(sp ³ )-H Bonds with Carbonyls In: Organic letters. 2019 ; Vol. 21, No. 8. pp. 2588-2592.

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abstract = " 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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