Beilstein Journal of Organic Chemistry p. 2747 - 2752 (2019)
Update date:2022-08-04
Topics:
Lee, Zachary
Jones, Brandon R.
Nkengbeza, Nyochembeng
Phillips, Michael
Valentine, Kayla
Stewart, Alexis
Sellers, Brandon
Shuber, Nicholas
Aiken, Karelle S.
An iodine-mediated hydration reaction of alkynes serves as a green alternative to metal-catalyzed procedures. Previous work has shown that this method works well with terminal alkynes on keto-functionalized scaffolds, including 1,3-dicarbonyls and their heteroatom analogues. It was hypothesized that the reaction proceeds through a 5-exo-dig neighboring group participation (NGP) cyclization and an α-iodo intermediate. The work described herein probes the existence of the intermediate through NMR investigations and explores the scope of the hydration process with internal alkynes. The NMR experiments confirm the existence of the α-iodo intermediate, and methodology studies demonstrate that alkyl-capped, asymmetric, internal alkynes undergo a regiospecific hydration, also via the 5-exo-dig NGP pathway.
View MoreSHAANXI TOP PHARM CHEMICAL CO.LTD
Contact:+86-029-85733403
Address:No.108 ,west sector,south er huan,xi'an,china
Nanjing Fubang Chemical Co.,Ltd
Contact:+86-25-83179199
Address:5F,Tianzheng international plaza,No399 Zhongyang Road ,Nanjing China
Zhangjiagang Golden Reach Fine Chemical Co.,LTD.
Contact:+86-512-6585 6968
Address:Changfu Road, Dongsha Chemical Industry Park, Zhangjiagang City, Jiangsu Province, China
Xiamen Kaijia Imp & Exp Co., Ltd.
Contact:86-592-5101177
Address:Room406 Luhui Building No. 65 Haitian Road Huli Xiamen,China.
Jiangsu Wanlong Chemical Co., Ltd.
website:http://www.wanlongchem.com
Contact:+86-511-86810993 0086-511-8681 0888;
Address:Quanzhou Town, Danyang City, Jiangsu
Doi:10.1016/S0040-4039(00)96266-X
(1987)Doi:10.1021/jo502572j
(2015)Doi:10.1055/s-1987-28073
(1987)Doi:10.1016/j.bmcl.2008.12.022
(2009)Doi:10.1016/j.tet.2008.12.038
(2009)Doi:10.1021/jo802714q
(2009)