Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans
Xin Cui; Xue Xu; Lukasz Wojtas; Martin M. Kim; X. Peter Zhang; Journal of the American Chemical Society 134 (2012) 19981–19984; doi:10.1021/ja309446n

data_4118990
_publ_section_title
;
 Regioselective Synthesis of Multisubstituted Furans via Metalloradical
 Cyclization of Alkynes with \a-Diazocarbonyls: Construction of
 Functionalized \a-Oligofurans
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19981
_journal_page_last               19984
_journal_paper_doi               10.1021/ja309446n
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C15 H18 Cl N3 O'
_chemical_formula_weight         291.77
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.321(3)
_cell_angle_beta                 93.281(3)
_cell_angle_gamma                92.027(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0249(4)
_cell_length_b                   10.3298(5)
_cell_length_c                   11.2418(5)
_cell_measurement_reflns_used    778
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.333
_cell_measurement_theta_min      4.15
_cell_volume                     771.92(7)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5399
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         4.15
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_T_max  0.8448
_exptl_absorpt_correction_T_min  0.7355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                1759
_reflns_number_total             2471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja309446n_si_003.cif
_cod_data_source_block           3bh
_cod_database_code               4118990