Nickel-Catalyzed Synthesis of Benzo[ b]naphtho[1,2- d]azepine via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes.Org Lett. 2018 10 05; 20(19):6229-6233.OL
Abstract
A Ni(II)-catalyzed tandem cyclopropane ring opening and radical alkylation of the aromatic ring using unactivated alkyl bromide-tethered alkylidenecyclopropanes (ACPs) have been described in this paper. This ring-forming process exhibits a broad substrate scope with a variety of primary alkyl bromides and aromatic rings, affording diversified benzo[ b]naphtho[1,2- d]azepine derivatives in moderate-to-excellent yields under mild conditions. Plausible reaction mechanisms have been proposed on the basis of several control experiments, including the deuterium labeling examinations. Further derivatization of the obtained polycyclic product has also been performed.
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Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
30251543
Citation
Jiang, Bo, et al. "Nickel-Catalyzed Synthesis of Benzo[ B]naphtho[1,2- D]azepine Via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes." Organic Letters, vol. 20, no. 19, 2018, pp. 6229-6233.
Jiang B, Liu JX, Wei Y, et al. Nickel-Catalyzed Synthesis of Benzo[ b]naphtho[1,2- d]azepine via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes. Org Lett. 2018;20(19):6229-6233.
Jiang, B., Liu, J. X., Wei, Y., & Shi, M. (2018). Nickel-Catalyzed Synthesis of Benzo[ b]naphtho[1,2- d]azepine via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes. Organic Letters, 20(19), 6229-6233. https://doi.org/10.1021/acs.orglett.8b02699
Jiang B, et al. Nickel-Catalyzed Synthesis of Benzo[ B]naphtho[1,2- D]azepine Via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes. Org Lett. 2018 10 5;20(19):6229-6233. PubMed PMID: 30251543.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Nickel-Catalyzed Synthesis of Benzo[ b]naphtho[1,2- d]azepine via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes.
AU - Jiang,Bo,
AU - Liu,Jia-Xin,
AU - Wei,Yin,
AU - Shi,Min,
Y1 - 2018/09/25/
PY - 2018/9/27/pubmed
PY - 2018/9/27/medline
PY - 2018/9/26/entrez
SP - 6229
EP - 6233
JF - Organic letters
JO - Org Lett
VL - 20
IS - 19
N2 - A Ni(II)-catalyzed tandem cyclopropane ring opening and radical alkylation of the aromatic ring using unactivated alkyl bromide-tethered alkylidenecyclopropanes (ACPs) have been described in this paper. This ring-forming process exhibits a broad substrate scope with a variety of primary alkyl bromides and aromatic rings, affording diversified benzo[ b]naphtho[1,2- d]azepine derivatives in moderate-to-excellent yields under mild conditions. Plausible reaction mechanisms have been proposed on the basis of several control experiments, including the deuterium labeling examinations. Further derivatization of the obtained polycyclic product has also been performed.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/30251543/Nickel_Catalyzed_Synthesis_of_Benzo[_b]naphtho[12__d]azepine_via_Intramolecular_Radical_Tandem_Cyclization_of_Alkyl_Bromide_Tethered_Alkylidenecyclopropanes_
DB - PRIME
DP - Unbound Medicine
ER -
