公开(公告)号：US09764995B2

公开(公告)日：2017-09-19

申请号：US15375747

申请日：2016-12-12

Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： Anton Toutov ,  Wenbo Liu ,  Brian M. Stoltz ,  Robert H. Grubbs ,  Kerry Betz ,  David P. Schuman

IPC: C07B47/00 ,  C07F7/08

CPC classification number: C07B47/00 ,  C07D209/12 ,  C07F5/04 ,  C07F7/0827

Abstract: The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates using at least alkoxide base, preferably a potassium alkoxide base and at least one organodisilane and (b) at least one alkoxide base. Both methods and compositions for affecting these transformations are disclosed.

公开(公告)号：US09556206B2

公开(公告)日：2017-01-31

申请号：US14841964

申请日：2015-09-01

Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： Anton Toutov ,  Kerry Betz ,  Brian M. Stoltz ,  Wenbo Liu ,  Robert H. Grubbs

IPC: C07F7/08 ,  C07J7/00 ,  C07J1/00 ,  C07J51/00

CPC classification number: C07F7/0827 ,  C07F17/02 ,  C07J1/0096 ,  C07J7/0005 ,  C07J51/00 ,  C07J75/00

Abstract: The present invention is directed to a mild, efficient, and general direct C(sp)-H bond silylation. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal alkynyl C—H bond, with a mixture of at least one organosilane and an alkali metal hydroxide, under conditions sufficient to form a silylated terminal alkynyl moiety. The methods are operable in the substantially absence of transition-metal compounds. The systems associated with these methods are also disclosed.

Abstract translation: 本发明涉及温和，有效和通用的直接C（sp）-H键甲硅烷基化。 各种实施方案包括方法，每种方法包括或基本上包括使至少一种包含末端炔基C-H键的有机底物与至少一种有机硅烷和碱金属氢氧化物的混合物在足以形成甲硅烷基化的末端炔基的条件下 部分。 所述方法在基本上不存在过渡金属化合物的情况下是可操作的。 还公开了与这些方法相关联的系统。

公开(公告)号：US11753421B2

公开(公告)日：2023-09-12

申请号：US17688122

申请日：2022-03-07

Applicant: California Institute of Technology

Inventor： Anton Toutov ,  Kerry Betz ,  Alexey Fedorov ,  Brian M. Stoltz ,  Wenbo Liu ,  Robert H. Grubbs

IPC: C07F7/08 ,  C07D209/12

CPC classification number: C07F7/0801 ,  C07D209/12 ,  C07F7/0827 ,  C07F7/0832

Abstract: The present disclosure describes methods for silylating aromatic derivatives, comprising the use of hydrosilanes and potassium hydroxide.

公开(公告)号：US20210047348A1

公开(公告)日：2021-02-18

申请号：US17074717

申请日：2020-10-20

Applicant: California Institute of Technology

Inventor： Anton Toutov ,  Kerry Betz ,  Alexey Fedorov ,  Brian M. Stoltz ,  Wenbo Liu ,  Robert H. Grubbs

IPC: C07F7/08 ,  C07D209/12

Abstract: The present disclosure describes methods for silylating aromatic derivatives, comprising the use of hydrosilanes and potassium hydroxide.

公开(公告)号：US20190048030A1

公开(公告)日：2019-02-14

申请号：US16159298

申请日：2018-10-12

Applicant: California Institute Of Technology

Inventor： Anton Toutov ,  Kerry Betz ,  Alexey Fedorov ,  Brian M. Stoltz ,  Wenbo Liu ,  Robert H. Grubbs

IPC: C07F7/08 ,  C07D209/12

Abstract: The present disclosure describes novel silylated heteroaromatic derivatives, including those prepared by methods comprising the use of hydrosilanes and at least one strong base, the definition of strong base now also including hydroxide, especially KOH.

公开(公告)号：US09556080B2

公开(公告)日：2017-01-31

申请号：US14972653

申请日：2015-12-17

Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： Anton Toutov ,  Wenbo Liu ,  Brian M. Stoltz ,  Robert H. Grubbs ,  Kerry Betz ,  David P. Schuman

IPC: C07B47/00 ,  C07F7/08 ,  C07D209/12

CPC classification number: C07B47/00 ,  C07D209/12 ,  C07F5/04 ,  C07F7/0827

Abstract: The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates, said system consisting essentially of a mixture of (a) at least one organodisilane and (b) at least alkoxide base, preferably a potassium alkoxide base, and said methods comprising contacting a quantity of the organic substrate with a mixture consisting essentially of (a) at least one organodisilane and (b) at least one alkoxide base, preferably a potassium alkoxide, under conditions sufficient to silylate the heteroaromatic substrate.

Abstract translation: 本发明描述了用于甲硅烷基化杂芳族有机底物的化学系统和方法，所述系统基本上由（a）至少一种有机硅烷和（b）至少烷氧基，优选烷醇钾碱的混合物组成，所述方法包括使 基本上由（a）至少一种有机硅烷和（b）至少一种醇盐碱，优选烷氧基钾，在足以使所述杂芳族底物甲硅烷基化的条件下混合的混合物的有机底物的量。