醋酸铋作为二硼化和三硼化吲哚顺序脱硼反应的催化剂
Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.
作者信息
Shen Fangyi, Tyagarajan Sriram, Perera Damith, Krska Shane W, Maligres Peter E, Smith Milton R, Maleczka Robert E
机构信息
Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
Department of Process Chemistry, Merck Research Laboratories , Rahway, New Jersey 07065, United States.
出版信息
Org Lett. 2016 Apr 1;18(7):1554-7. doi: 10.1021/acs.orglett.6b00356. Epub 2016 Mar 21.
Abstract
Bismuth(III) acetate is a safe, inexpensive, and selective facilitator of sequential protodeboronations, which when used in conjunction with Ir-catalyzed borylations allows access to a diversity of borylated indoles. The versatility of combining Ir-catalyzed borylations with Bi(III)-catalyzed protodeboronation is demonstrated by selectively converting 6-fluoroindole into products with Bpin groups at the 4-, 5-, 7-, 2,7-, 4,7-, 3,5-, and 2,4,7-positions and the late-stage functionalization of sumatriptan.
摘要
醋酸铋(III)是一种安全、廉价且具有选择性的连续去硼化促进剂，与铱催化的硼化反应结合使用时，可用于合成多种硼化吲哚。铱催化的硼化反应与铋(III)催化的去硼化反应相结合的多功能性体现在，能够将6-氟吲哚选择性地转化为在4-、5-、7-、2,7-、4,7-、3,5-和2,4,7-位带有硼酸频哪醇酯基团的产物，以及舒马曲坦的后期官能团化反应中。
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