Tags

Type your tag names separated by a space and hit enter

Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-a]isoquinolines.
Org Lett. 2019 09 20; 21(18):7284-7288.OL

Abstract

A novel palladium-catalyzed cascade cyclization of alkene-tethered aryl halides with o-bromobenzoic acids is described, which provides an efficient avenue for building various fused hexacyclic scaffolds containing indolo[2,1-a]isoquinoline in moderate to excellent yield. The method enables the construction of three C-C bonds through an intramolecular carbopalladation, C-H activation, and a decarboxylation sequence. Furthermore, dihydrocyclohepta[de]naphthalene-fused indolo[2,1-a]isoquinolines can be synthesized in moderate yield by constructing a seven-membered ring.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Yang X
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Lu H
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Zhu X
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Zhou L
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Deng G
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Yang Y
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Liang Y
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

31502462

Citation

Yang, Xiumei, et al. "Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides With o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-a]isoquinolines." Organic Letters, vol. 21, no. 18, 2019, pp. 7284-7288.
Yang X, Lu H, Zhu X, et al. Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-a]isoquinolines. Org Lett. 2019;21(18):7284-7288.
Yang, X., Lu, H., Zhu, X., Zhou, L., Deng, G., Yang, Y., & Liang, Y. (2019). Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-a]isoquinolines. Organic Letters, 21(18), 7284-7288. https://doi.org/10.1021/acs.orglett.9b02541
Yang X, et al. Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides With o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-a]isoquinolines. Org Lett. 2019 09 20;21(18):7284-7288. PubMed PMID: 31502462.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-a]isoquinolines. AU - Yang,Xiumei, AU - Lu,Haiyan, AU - Zhu,Xiaoming, AU - Zhou,Liwei, AU - Deng,Guobo, AU - Yang,Yuan, AU - Liang,Yun, Y1 - 2019/09/10/ PY - 2019/9/11/pubmed PY - 2019/9/11/medline PY - 2019/9/11/entrez SP - 7284 EP - 7288 JF - Organic letters JO - Org Lett VL - 21 IS - 18 N2 - A novel palladium-catalyzed cascade cyclization of alkene-tethered aryl halides with o-bromobenzoic acids is described, which provides an efficient avenue for building various fused hexacyclic scaffolds containing indolo[2,1-a]isoquinoline in moderate to excellent yield. The method enables the construction of three C-C bonds through an intramolecular carbopalladation, C-H activation, and a decarboxylation sequence. Furthermore, dihydrocyclohepta[de]naphthalene-fused indolo[2,1-a]isoquinolines can be synthesized in moderate yield by constructing a seven-membered ring. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31502462/Palladium_Catalyzed_Cascade_Cyclization_of_Alkene_Tethered_Aryl_Halides_with_o_Bromobenzoic_Acids:_Access_to_Diverse_Fused_Indolo[21_a]isoquinolines_ DB - PRIME DP - Unbound Medicine ER -