Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-iodopyridones, alkynes, and organic halides.
Bossharth, Emmanuel; Desbordes, Philippe; Monteiro, Nuno; Balme, Geneviève; Organic letters 5 (2003) 2441–2444; doi:10.1021/ol034644y

data_1507327
_publ_section_title
;
 Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by
 one-pot coupling of 3-iodopyridones, alkynes, and organic halides.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2441
_journal_page_last               2444
_journal_paper_doi               10.1021/ol034644y
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C20 H14 F N O2'
_chemical_formula_weight         319.32
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.51(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.532(3)
_cell_length_b                   12.935(3)
_cell_length_c                   9.831(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1592.1(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3586
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1987P)^2^+0.5129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2507
_reflns_number_gt                2472
_reflns_number_total             3586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034644ysi20030528_100951.cif
_cod_data_source_block           eb252f
_cod_database_code               1507327