Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

TY - JOUR

T1 - Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

AU - Johansen, Martin B.

AU - Gedde, Oliver R.

AU - Mayer, Thea S.

AU - Skrydstrup, Troels

PY - 2020/6

Y1 - 2020/6

N2 - We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.

AB - We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.

UR - http://www.scopus.com/inward/record.url?scp=85085612584&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01117

DO - 10.1021/acs.orglett.0c01117

M3 - Journal article

C2 - 32391697

AN - SCOPUS:85085612584

SN - 1523-7060

VL - 22

SP - 4068

EP - 4072

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -