PMID- 31731202
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20200928
IS  - 2589-0042 (Electronic)
IS  - 2589-0042 (Linking)
VI  - 21
DP  - 2019 Nov 22
TI  - From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of 
      C(sp(3))-H Bond.
PG  - 650-663
LID - S2589-0042(19)30438-9 [pii]
LID - 10.1016/j.isci.2019.10.057 [doi]
AB  - Heterocycles are prevalent constituents of many marketing drugs and biologically 
      active molecules to meet modern medical challenges. Isocyanide insertion into 
      C(sp(3))-H bonds is challenging especially for the construction of quaternary 
      carbon centers. Herein, we describe an efficient strategy for the synthesis of 
      alpha-iminonitrile substituted isochromans and tetrahydroisoquinolines (THIQs) with 
      quaternary carbon centers through silver-triflate-mediated sequential isocyanide 
      insertion of C(sp(3))-H bonds, where isocyanide acts as the crucial "CN" and 
      "imine" sources. The produced alpha-iminonitriles have extensive applications as 
      valuable synthetic building blocks for pharmacologically interesting 
      heterocycles. This protocol could be further applied for the synthesis of 
      iminonitrile-decorated phenanthridines and azapyrene. Interestingly, a remarkable 
      aggregation-induced emission (AIE) effect was first observed for an 
      iminonitrile-decorated pyrene derivative, which may open a particular area for 
      iminonitrile applications in materials science.
CI  - Copyright (c) 2019 The Author(s). Published by Elsevier Inc. All rights reserved.
FAU - Chi, Huiwen
AU  - Chi H
AD  - Department of Chemistry, Innovative Drug Research Center, Shanghai University, 
      Shanghai 200444, China.
FAU - Li, Hao
AU  - Li H
AD  - Department of Chemistry, Innovative Drug Research Center, Shanghai University, 
      Shanghai 200444, China.
FAU - Liu, Bingxin
AU  - Liu B
AD  - Department of Chemistry, Innovative Drug Research Center, Shanghai University, 
      Shanghai 200444, China.
FAU - Ye, Rongxuan
AU  - Ye R
AD  - Department of Chemistry, Innovative Drug Research Center, Shanghai University, 
      Shanghai 200444, China; Qianweichang College, Shanghai University, Shanghai 
      200444, China.
FAU - Wang, Haoyang
AU  - Wang H
AD  - State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic 
      Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
FAU - Guo, Yin-Long
AU  - Guo YL
AD  - State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic 
      Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
FAU - Tan, Qitao
AU  - Tan Q
AD  - Department of Chemistry, Innovative Drug Research Center, Shanghai University, 
      Shanghai 200444, China. Electronic address: qttan@shu.edu.cn.
FAU - Xu, Bin
AU  - Xu B
AD  - Department of Chemistry, Innovative Drug Research Center, Shanghai University, 
      Shanghai 200444, China; State Key Laboratory of Organometallic Chemistry, 
      Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 
      200032, China. Electronic address: xubin@shu.edu.cn.
LA  - eng
PT  - Journal Article
DEP - 20191101
PL  - United States
TA  - iScience
JT  - iScience
JID - 101724038
PMC - PMC6859232
OTO - NOTNLM
OT  - Materials Chemistry
OT  - Optical Property
OT  - Organic Synthesis
COIS- The authors declare no competing interests.
EDAT- 2019/11/16 06:00
MHDA- 2019/11/16 06:01
PMCR- 2019/11/01
CRDT- 2019/11/16 06:00
PHST- 2019/08/06 00:00 [received]
PHST- 2019/10/25 00:00 [revised]
PHST- 2019/10/27 00:00 [accepted]
PHST- 2019/11/16 06:00 [pubmed]
PHST- 2019/11/16 06:01 [medline]
PHST- 2019/11/16 06:00 [entrez]
PHST- 2019/11/01 00:00 [pmc-release]
AID - S2589-0042(19)30438-9 [pii]
AID - 10.1016/j.isci.2019.10.057 [doi]
PST - ppublish
SO  - iScience. 2019 Nov 22;21:650-663. doi: 10.1016/j.isci.2019.10.057. Epub 2019 Nov 
      1.